diff --git a/.gitlab-ci.yml b/.gitlab-ci.yml
index 13aebbe74..514d146e7 100644
--- a/.gitlab-ci.yml
+++ b/.gitlab-ci.yml
@@ -103,8 +103,7 @@ test-utils:
     - printf '\e[0K%s:%s:%s\r\e[0K\n' section_end "$(date +%s)" install_extra_deps
 
     # See apparmor/apparmor#221
-    - make -C parser/tst gen_dbus
-    - make -C parser/tst gen_xtrans
+    - make -C parser/tst gen_tests
     - make -C utils check
     - make -C utils/test coverage-regression
   artifacts:
diff --git a/parser/apparmor.d.pod b/parser/apparmor.d.pod
index 373ddade4..237c1583a 100644
--- a/parser/apparmor.d.pod
+++ b/parser/apparmor.d.pod
@@ -72,10 +72,12 @@ B<PROFILE FILE> = ( [ I<PREAMBLE> ] [ I<PROFILE> ] )*
 B<PREAMBLE> = ( I<COMMENT> | I<VARIABLE ASSIGNMENT> | I<ALIAS RULE> | I<INCLUDE> | I<ABI> )*
   Variable assignment and alias rules must come before the profile.
 
-B<VARIABLE ASSIGNMENT> = I<VARIABLE> ('=' | '+=') (space separated values)
+B<VARIABLE ASSIGNMENT> = ( I<VARIABLE> | I<BOOL_VAR> ) ('=' | '+=') (space separated values)
 
 B<VARIABLE> = '@{' I<ALPHA> [ ( I<ALPHANUMERIC> | '_' ) ... ] '}'
 
+B<BOOL_VAR> = '${' I<ALPHA> [ ( I<ALPHANUMERIC> | '_' ) ... ] '}'
+
 B<ALIAS RULE> = 'alias' I<ABS PATH> '-E<gt>' I<REWRITTEN ABS PATH> ','
 
 B<INCLUDE> = ( '#include' | 'include' ) [ 'if exists' ] ( I<ABS PATH> | I<MAGIC PATH> )
@@ -130,7 +132,7 @@ B<LINE RULES> = ( I<COMMENT> | I<INCLUDE> ) [ '\r' ] '\n'
 
 B<COMMA RULES> = ( I<CAPABILITY RULE> | I<NETWORK RULE> | I<MOUNT RULE> | I<PIVOT ROOT RULE> | I<UNIX RULE> | I<FILE RULE> | I<LINK RULE> | I<CHANGE_PROFILE RULE> | I<RLIMIT RULE> | I<DBUS RULE> | I<MQUEUE RULE> | I<IO_URING RULE> | I<USERNS RULE> | I<ALL RULE>)
 
-B<BLOCK RULES> = ( I<SUBPROFILE> | I<HAT> | I<QUALIFIER BLOCK> )
+B<BLOCK RULES> = ( I<SUBPROFILE> | I<HAT> | I<QUALIFIER BLOCK> | I<IF_BLOCK> )
 
 B<SUBPROFILE> = 'profile' I<PROFILE NAME> [ I<ATTACHMENT SPECIFICATION> ] [ I<PROFILE FLAG CONDS> ] '{' ( I<RULES> )* '}'
 
@@ -142,6 +144,16 @@ B<QUALIFIER BLOCK> = I<QUALIFIERS> I<BLOCK>
 
 B<INTEGER> = (+ | -)? [[:digit:]]+
 
+B<IF_BLOCK> = 'if' I<EXPR> I<BLOCK> [ ( 'else' 'if'  I<EXPR> I<BLOCK> )* ] [ 'else' I<BLOCK> ]
+
+B<EXPR> = ( I<EXPR> ( 'and' | 'or' ) I<EXPR> | 'not' I<EXPR> | '(' I<EXPR> ')' | I<FACTOR> )
+
+B<FACTOR> = ( 'defined' I<VARIABLE> | [ 'defined' ] I<BOOL_VAR> | ( I<TEXT> | I<VARIABLE> ) I<OPERATOR> ( I<TEXT> | I<VARIABLE> ) )
+
+B<OPERATOR> = ( 'in' | '==' | '!=' | '>' | '>=' | '<' | '<=' )
+
+B<BLOCK> = '{' ( I<RULES> )* '}'
+
 B<ACCESS TYPE> = ( 'allow' | 'deny' )
 
 B<QUALIFIERS> = [ 'priority' '=' <INTEGER> ] [ 'audit' ] [ I<ACCESS TYPE> ]
@@ -1880,6 +1892,13 @@ example) is collapsed.
 
 =back
 
+=head3 Boolean Variables
+
+In addition to the set variables AppArmor supports boolean
+variables. These begin with a B<$> and can only be used in conditional
+expressions. Boolean variables provide a convenient way to
+enable/disable policy rules that have been wrapped in the proper if
+condition.
 
 =head2 Alias rules
 
@@ -2203,6 +2222,107 @@ An example AppArmor profile:
 	  }
   	}
 
+=head2 Conditional rules
+
+AppArmor provides a mechanism to conditionally enable and disable
+rules in a profile. Rules that are to be conditionally used can be
+wrapped in an I<if> condition block with the condition expression
+being controlled by setting variable values.
+
+The condition expression can be composed of variables, boolean
+variables, a B<defined> check, the comparison operators B<in>, B<==>,
+B<!=>, B<>>, B<>=>, B<<>, and B<<=>, open '(' and close ')' parentheses,
+and the boolean operators B<and>, B<or>, and B<not>. Boolean operators
+are evaluated left to write with priority in order of the
+following list.
+
+=over 4
+
+=item B<in>	- tests whether the left text or variable is a subset of
+the text or variable on the right. The subset check is done by a full
+match, therefore partial string matches would not evaluate to true.
+
+=item B<==>	- tests whether both text or variable evaluate to the same
+value.
+
+=item B<!=>	- tests whether both text or variable evaluate to
+different values.
+
+=item B<>>	- tests whether the left text or variable is greater than
+the right text or variable.
+Comparisons between integers and set variables will fail to compile
+unless the variable contents are exactly one value, an integer. Other
+comparison will be strictly lexicographical.
+
+=item B<>=>	- tests whether the left text or variable is greater than
+or equal to the right text or variable.
+Comparisons between integers and set variables will fail to compile
+unless the variable contents are exactly one value, an integer. Other
+comparison will be strictly lexicographical.
+
+=item B<<>	- tests whether the left text or variable is lesser than
+the right text or variable.
+Comparisons between integers and set variables will fail to compile
+unless the variable contents are exactly one value, an integer. Other
+comparison will be strictly lexicographical.
+
+=item B<<=>	- tests whether the left text or variable is lesser than
+or equal to the right text or variable.
+Comparisons between integers and set variables will fail to compile
+unless the variable contents are exactly one value, an integer. Other
+comparison will be strictly lexicographical.
+
+=item B<defined> - tests whether the following variable or boolean
+variable has been defined/created.
+
+=item B<parentheses> - open '(' and close ')' paretheses are used to
+group operations by priority.
+
+=item B<not>	- boolean B<not> operator, negates the value of the
+following expression.
+
+=item B<and>	- boolean B<and> operator, both expressions being
+combined with B<and> must be true for the result to be true.
+
+=item B<or>	- boolean B<or> operator, either one or both expressions
+being combined with B<or> can be true for the result to be true.
+
+=back
+
+An example of a profile conditional
+
+	if ${distro_mods} and defined @{HOME} {
+	  /@{HOME}/.foo_file  rw,
+	} else {
+	  /home/*/.foo_file  rw,
+	}
+
+Since lexicographical comparisons using the B<>>, B<>=>, B<<>, B<<=>
+operators could lead to mistakes when comparing integers, comparisons
+between variables and integers will fail to compile unless the
+variable contains an integer.
+
+Eg.
+
+	@{BAR} = /home/user/ /home/user2/
+	@{BAR} += /home/user3/
+	@{TEST_VERSION} = 2
+	@{BAZ} = 10
+
+	/usr/bin/foo {
+	  if /home/user/ in @{BAR} {
+	    /** r,
+	  }
+	  if @{TEST_VERSION} >= @{BAZ} {
+	    /** w,
+	  } else if 10 > @{TEST_VERSION} {
+	    /** rw,
+	  }
+	  if @{BAZ} <= 10 {
+	    /** rw,
+	  }
+	}
+
 =head1 FILES
 
 =over 4
diff --git a/parser/cond_expr.cc b/parser/cond_expr.cc
index f601618a1..ffa784db8 100644
--- a/parser/cond_expr.cc
+++ b/parser/cond_expr.cc
@@ -16,6 +16,8 @@
  *   Ltd.
  */
 
+#include <algorithm>
+
 #include "cond_expr.h"
 #include "parser.h"
 #include "symtab.h"
@@ -25,17 +27,16 @@ cond_expr::cond_expr(bool result):
 {
 }
 
-cond_expr::cond_expr(const char *var, bool defined)
+cond_expr::cond_expr(const char *var, cond_op op)
 {
 	variable *ref;
-	if (!defined) {
+	if (op == BOOLEAN_OP) {
 		ref = symtab::get_boolean_var(var);
 		if (!ref) {
-			/* FIXME check for set var */
 			yyerror(_("Unset boolean variable %s used in if-expression"), var);
 		}
 		result = ref->boolean;
-	} else {
+	} else if (op == DEFINED_OP) {
 		ref = symtab::get_set_var(var);
 		if (!ref) {
 			result = false;
@@ -43,5 +44,106 @@ cond_expr::cond_expr(const char *var, bool defined)
 			PDEBUG("Matched: defined set expr %s value %s\n", var, ref->expanded.begin()->c_str());
 			result = true;
 		}
+	} else
+		PERROR("Invalid operation for if-expression");
+}
+
+/* variables passed in conditionals can be variables or values.
+
+   if the string passed has the formatting of a variable (@{}), then
+   we should look for it in the symtab. if it's present in the symtab,
+   expand its values and return the expanded set. if it's not present
+   in the symtab, we should error out. if the string passed does not
+   have the formatting of a variable, we should treat it as if it was
+   a value. add it to a set and return it so comparisons can be made.
+*/
+std::set<std::string> cond_expr::get_set(const char *var)
+{
+	char *var_name = variable::process_var(var);
+	if (!var_name) {
+		/* not a variable */
+		return {var};
+	}
+	variable *ref = symtab::lookup_existing_symbol(var_name);
+	free(var_name);
+	if (!ref) {
+		yyerror(_("Error retrieving variable %s"), var);
+	}
+	if (ref->expand_variable() != 0) {
+		/* expand_variable prints error messages already, so
+		 * exit quietly here */
+		exit(1);
+	}
+	return ref->expanded;
+}
+
+template <typename T>
+void cond_expr::compare(cond_op op, T lhs, T rhs)
+{
+	switch (op) {
+	case GT_OP:
+		result = lhs > rhs;
+		break;
+	case GE_OP:
+		result = lhs >= rhs;
+		break;
+	case LT_OP:
+		result = lhs < rhs;
+		break;
+	case LE_OP:
+		result = lhs <= rhs;
+		break;
+	default:
+		PDEBUG("Invalid op\n");
+	}
+}
+
+bool nullstr(char *p)
+{
+	return p && !(*p);
+}
+
+long str_set_to_long(std::set<std::string> &src, char **endptr)
+{
+	long converted_src = 0;
+	errno = 0;
+	if (src.size() == 1 && !src.begin()->empty())
+		converted_src = strtol(src.begin()->c_str(), endptr, 0);
+	if (errno == ERANGE)
+		yyerror(_("Value out of valid range\n"));
+	return converted_src;
+}
+
+cond_expr::cond_expr(const char *lhv, cond_op op, const char *rhv)
+{
+	std::set<std::string> lhs = get_set(lhv);
+	std::set<std::string> rhs = get_set(rhv);
+	char *p_lhs = NULL, *p_rhs = NULL;
+	long converted_lhs = 0, converted_rhs = 0;
+
+	if (op == IN_OP) {
+		/* if lhs is a subset of rhs */
+		result = std::includes(rhs.begin(), rhs.end(),
+				       lhs.begin(), lhs.end());
+		return;
+	} else if (op == EQ_OP) {
+		result = lhs == rhs;
+		return;
+	} else if (op == NE_OP) {
+		result = lhs != rhs;
+		return;
+	}
+
+	converted_lhs = str_set_to_long(lhs, &p_lhs);
+	converted_rhs = str_set_to_long(rhs, &p_rhs);
+
+	if (!nullstr(p_lhs) && !nullstr(p_rhs)) {
+		/* sets */
+		compare(op, lhs, rhs);
+	} else if (nullstr(p_lhs) && nullstr(p_rhs)) {
+		/* numbers */
+		compare(op, converted_lhs, converted_rhs);
+	} else {
+		yyerror(_("Can only compare numbers with numbers\n"));
 	}
 }
diff --git a/parser/cond_expr.h b/parser/cond_expr.h
index 13bd8d524..9ab405e47 100644
--- a/parser/cond_expr.h
+++ b/parser/cond_expr.h
@@ -19,12 +19,31 @@
 #ifndef __AA_COND_EXPR_H
 #define __AA_COND_EXPR_H
 
+#include <set>
+#include <string>
+
+typedef enum {
+	EQ_OP,
+	NE_OP,
+	IN_OP,
+	GT_OP,
+	GE_OP,
+	LT_OP,
+	LE_OP,
+	BOOLEAN_OP,
+	DEFINED_OP,
+} cond_op;
+
 class cond_expr {
 private:
 	bool result;
 public:
 	cond_expr(bool result);
-	cond_expr(const char *var, bool defined);
+	cond_expr(const char *var, cond_op op);
+	cond_expr(const char *var, cond_op op, const char *cond_id);
+	std::set<std::string> get_set(const char *var);
+	template <typename T>
+	void compare(cond_op op, T lhs, T rhs);
 	virtual ~cond_expr()
 	{
 	};
diff --git a/parser/parser_lex.l b/parser/parser_lex.l
index f7b3ff4db..6664f63bc 100644
--- a/parser/parser_lex.l
+++ b/parser/parser_lex.l
@@ -299,7 +299,11 @@ ADD_ASSIGN	\+=
 ARROW		->
 LT_EQUAL	<=
 LT		<
+GT_EQUAL	>=
 GT		>
+EQ_OP		==
+NE_OP		!=
+IN_OP		in
 
 /* IF adding new state please update state_names table and default rule (just
  * above the state_names table) at the eof.
@@ -336,6 +340,8 @@ GT		>
 %x MQUEUE_MODE
 %x IOURING_MODE
 %x INTEGER_MODE
+%x EXPR_MODE
+
 %%
 
 %{
@@ -347,7 +353,7 @@ GT		>
 	}
 %}
 
-<INITIAL,SUB_ID_WS,INCLUDE,INCLUDE_EXISTS,LIST_VAL_MODE,EXTCOND_MODE,LIST_COND_VAL,LIST_COND_PAREN_VAL,LIST_COND_MODE,EXTCONDLIST_MODE,ASSIGN_MODE,NETWORK_MODE,CHANGE_PROFILE_MODE,RLIMIT_MODE,MOUNT_MODE,DBUS_MODE,SIGNAL_MODE,PTRACE_MODE,UNIX_MODE,ABI_MODE,USERNS_MODE,MQUEUE_MODE,IOURING_MODE,INTEGER_MODE>{
+<INITIAL,SUB_ID_WS,INCLUDE,INCLUDE_EXISTS,LIST_VAL_MODE,EXTCOND_MODE,LIST_COND_VAL,LIST_COND_PAREN_VAL,LIST_COND_MODE,EXTCONDLIST_MODE,ASSIGN_MODE,NETWORK_MODE,CHANGE_PROFILE_MODE,RLIMIT_MODE,MOUNT_MODE,DBUS_MODE,SIGNAL_MODE,PTRACE_MODE,UNIX_MODE,ABI_MODE,USERNS_MODE,MQUEUE_MODE,IOURING_MODE,INTEGER_MODE,EXPR_MODE>{
 	{WS}+	{  DUMP_PREPROCESS; /* Ignoring whitespace */ }
 }
 
@@ -647,6 +653,41 @@ GT		>
 	}
 }
 
+<INITIAL,EXPR_MODE>{
+	{SET_VARIABLE}	{
+		yylval.set_var = strdup(yytext);
+		RETURN_TOKEN(TOK_SET_VAR);
+	}
+
+	{BOOL_VARIABLE}	{
+		yylval.bool_var = strdup(yytext);
+		RETURN_TOKEN(TOK_BOOL_VAR);
+	}
+}
+
+<EXPR_MODE>{
+	{OPEN_BRACE}	{ POP_AND_RETURN(TOK_OPEN); }
+
+	{OPEN_PAREN}	{ RETURN_TOKEN(TOK_OPENPAREN); }
+	{CLOSE_PAREN}	{ RETURN_TOKEN(TOK_CLOSEPAREN); }
+	and		{ RETURN_TOKEN(TOK_AND); }
+	or		{ RETURN_TOKEN(TOK_OR); }
+	not		{ RETURN_TOKEN(TOK_NOT); }
+	defined	{ RETURN_TOKEN(TOK_DEFINED); }
+	{EQ_OP}	{ RETURN_TOKEN(TOK_EQ_OP); }
+	{NE_OP}	{ RETURN_TOKEN(TOK_NE_OP); }
+	{IN_OP}	{ RETURN_TOKEN(TOK_IN_OP); }
+	{GT}		{ RETURN_TOKEN(TOK_GT); }
+	{GT_EQUAL}	{ RETURN_TOKEN(TOK_GE); }
+	{LT}		{ RETURN_TOKEN(TOK_LT); }
+	{LT_EQUAL}	{ RETURN_TOKEN(TOK_LE); }
+
+	({IDS_NOEQ}|{LABEL}|{QUOTED_ID}) {
+		yylval.id = processid(yytext, yyleng);
+		RETURN_TOKEN(TOK_ID);
+	}
+}
+
 #include{WS}+if{WS}+exists/{WS}.*\r?\n	{
 	/* Don't use PUSH() macro here as we don't want #include echoed out.
 	 * It needs to be handled specially
@@ -694,16 +735,6 @@ all/({WS}|[^[:alnum:]_]) {
 
 {ADD_ASSIGN}	{ PUSH_AND_RETURN(ASSIGN_MODE, TOK_ADD_ASSIGN); }
 
-{SET_VARIABLE}	{
-	yylval.set_var = strdup(yytext);
-	RETURN_TOKEN(TOK_SET_VAR);
-}
-
-{BOOL_VARIABLE}	{
-	yylval.bool_var = strdup(yytext);
-	RETURN_TOKEN(TOK_BOOL_VAR);
-}
-
 {OPEN_BRACE}	{ RETURN_TOKEN(TOK_OPEN); }
 
 {CLOSE_BRACE}	{ RETURN_TOKEN(TOK_CLOSE); }
@@ -772,6 +803,9 @@ all/({WS}|[^[:alnum:]_]) {
 	case TOK_MQUEUE:
 		state = MQUEUE_MODE;
 		break;
+	case TOK_IF:
+		state = EXPR_MODE;
+		break;
 	default: /* nothing */
 		break;
 	}
@@ -786,14 +820,14 @@ all/({WS}|[^[:alnum:]_]) {
 	}
 }
 
-<INITIAL,SUB_ID_WS,INCLUDE,INCLUDE_EXISTS,LIST_VAL_MODE,EXTCOND_MODE,LIST_COND_VAL,LIST_COND_PAREN_VAL,LIST_COND_MODE,EXTCONDLIST_MODE,NETWORK_MODE,CHANGE_PROFILE_MODE,RLIMIT_MODE,MOUNT_MODE,DBUS_MODE,SIGNAL_MODE,PTRACE_MODE,UNIX_MODE,ABI_MODE,USERNS_MODE,MQUEUE_MODE,IOURING_MODE>{
+<INITIAL,SUB_ID_WS,INCLUDE,INCLUDE_EXISTS,LIST_VAL_MODE,EXTCOND_MODE,LIST_COND_VAL,LIST_COND_PAREN_VAL,LIST_COND_MODE,EXTCONDLIST_MODE,NETWORK_MODE,CHANGE_PROFILE_MODE,RLIMIT_MODE,MOUNT_MODE,DBUS_MODE,SIGNAL_MODE,PTRACE_MODE,UNIX_MODE,ABI_MODE,USERNS_MODE,MQUEUE_MODE,IOURING_MODE,EXPR_MODE>{
 	\r?\n	{
 		DUMP_PREPROCESS;
 		current_lineno++;
 	}
 }
 
-<INITIAL,SUB_ID,SUB_ID_WS,SUB_VALUE,LIST_VAL_MODE,EXTCOND_MODE,LIST_COND_VAL,LIST_COND_PAREN_VAL,LIST_COND_MODE,EXTCONDLIST_MODE,ASSIGN_MODE,NETWORK_MODE,CHANGE_PROFILE_MODE,MOUNT_MODE,DBUS_MODE,SIGNAL_MODE,PTRACE_MODE,UNIX_MODE,RLIMIT_MODE,INCLUDE,INCLUDE_EXISTS,ABI_MODE,USERNS_MODE,MQUEUE_MODE,IOURING_MODE>{
+<INITIAL,SUB_ID,SUB_ID_WS,SUB_VALUE,LIST_VAL_MODE,EXTCOND_MODE,LIST_COND_VAL,LIST_COND_PAREN_VAL,LIST_COND_MODE,EXTCONDLIST_MODE,ASSIGN_MODE,NETWORK_MODE,CHANGE_PROFILE_MODE,MOUNT_MODE,DBUS_MODE,SIGNAL_MODE,PTRACE_MODE,UNIX_MODE,RLIMIT_MODE,INCLUDE,INCLUDE_EXISTS,ABI_MODE,USERNS_MODE,MQUEUE_MODE,IOURING_MODE,EXPR_MODE>{
 	(.|\n)	{
 		DUMP_PREPROCESS;
 		/* Something we didn't expect */
@@ -832,4 +866,5 @@ unordered_map<int, string> state_names = {
 	STATE_TABLE_ENT(MQUEUE_MODE),
 	STATE_TABLE_ENT(IOURING_MODE),
 	STATE_TABLE_ENT(INTEGER_MODE),
+	STATE_TABLE_ENT(EXPR_MODE),
 };
diff --git a/parser/parser_misc.c b/parser/parser_misc.c
index 4634b3f43..12a71306f 100644
--- a/parser/parser_misc.c
+++ b/parser/parser_misc.c
@@ -134,6 +134,8 @@ static const unordered_map<string, int> keyword_table = {
 	{"sqpoll",		TOK_SQPOLL},
 	{"all",			TOK_ALL},
 	{"priority",		TOK_PRIORITY},
+	{"and",			TOK_AND},
+	{"or",			TOK_OR},
 };
 
 /* glibc maps bsd ofile to nofile but musl does not. */
diff --git a/parser/parser_yacc.y b/parser/parser_yacc.y
index 0e4e4a643..0086dc59c 100644
--- a/parser/parser_yacc.y
+++ b/parser/parser_yacc.y
@@ -152,6 +152,14 @@ static void abi_features(char *filename, bool search);
 %token TOK_SQPOLL
 %token TOK_ALL
 %token TOK_PRIORITY
+%token TOK_AND
+%token TOK_OR
+%token TOK_EQ_OP
+%token TOK_NE_OP
+%token TOK_IN_OP
+%token TOK_GT
+%token TOK_GE
+%token TOK_LT
 
  /* rlimits */
 %token TOK_RLIMIT
@@ -270,6 +278,9 @@ static void abi_features(char *filename, bool search);
 %type <var_val>	TOK_VALUE
 %type <val_list> valuelist
 %type <cond> expr
+%type <cond> term
+%type <cond> notfactor
+%type <cond> factor
 %type <id>	id_or_var
 %type <id>	opt_id_or_var
 %type <boolean> opt_subset_flag
@@ -942,37 +953,134 @@ cond_rule: TOK_IF expr block TOK_ELSE cond_rule
 		$$ = ret;
 	}
 
-expr:	TOK_NOT expr
+
+expr:   expr TOK_OR term
+	{
+		cond_expr *conds = new cond_expr($1->eval() || $3->eval());
+		delete $1;
+		delete $3;
+		$$ = conds;
+	}
+	| term
+	{
+		$$ = $1;
+	}
+
+term:	term TOK_AND notfactor
+	{
+		cond_expr *conds = new cond_expr($1->eval() && $3->eval());
+		delete $1;
+		delete $3;
+		$$ = conds;
+	}
+	| notfactor
+	{
+		$$ = $1;
+	}
+
+notfactor:	TOK_NOT notfactor
 	{
 		cond_expr *conds = new cond_expr(!$2->eval());
 		delete $2;
 		$$ = conds;
 	}
-
-expr:	TOK_BOOL_VAR
+	| factor
 	{
-		cond_expr *conds = new cond_expr($1, false);
+		$$ = $1;
+	}
+
+factor:	TOK_BOOL_VAR
+	{
+		cond_expr *conds = new cond_expr($1, BOOLEAN_OP);
 		PDEBUG("Matched: boolean expr %s value: %d\n", $1, conds->eval());
 		$$ = conds;
 		free($1);
 	}
 
-expr:	TOK_DEFINED TOK_SET_VAR
+factor:	TOK_DEFINED TOK_SET_VAR
 	{
-		cond_expr *conds = new cond_expr($2, true);
+		cond_expr *conds = new cond_expr($2, DEFINED_OP);
 		PDEBUG("Matched: defined set expr %s value %d\n", $2, conds->eval());
 		$$ = conds;
 		free($2);
 	}
 
-expr:	TOK_DEFINED TOK_BOOL_VAR
+factor:	TOK_DEFINED TOK_BOOL_VAR
 	{
-		cond_expr *conds = new cond_expr($2, false);
+		cond_expr *conds = new cond_expr($2, DEFINED_OP);
 		PDEBUG("Matched: defined set expr %s value %d\n", $2, conds->eval());
 		$$ = conds;
 		free($2);
 	}
 
+factor:   TOK_OPENPAREN expr TOK_CLOSEPAREN
+	{
+		$$ = $2;
+	}
+
+factor:	id_or_var TOK_EQ_OP id_or_var
+	{
+		cond_expr *conds = new cond_expr($1, EQ_OP, $3);
+		PDEBUG("Matched: equal set expr %s == %s value %d\n", $1, $3, conds->eval());
+		$$ = conds;
+		free($1);
+		free($3);
+	}
+
+factor:	id_or_var TOK_NE_OP id_or_var
+	{
+		cond_expr *conds = new cond_expr($1, NE_OP, $3);
+		PDEBUG("Matched: not equal set expr %s != %s value %d\n", $1, $3, conds->eval());
+		$$ = conds;
+		free($1);
+		free($3);
+	}
+
+factor:	id_or_var TOK_IN_OP id_or_var
+	{
+		cond_expr *conds = new cond_expr($1, IN_OP, $3);
+		PDEBUG("Matched: in set expr %s in %s value %d\n", $1, $3, conds->eval());
+		$$ = conds;
+		free($1);
+		free($3);
+	}
+
+factor:	id_or_var TOK_GT id_or_var
+	{
+		cond_expr *conds = new cond_expr($1, GT_OP, $3);
+		PDEBUG("Matched: greater set expr %s > %s value %d\n", $1, $3, conds->eval());
+		$$ = conds;
+		free($1);
+		free($3);
+	}
+
+factor:	id_or_var TOK_GE id_or_var
+	{
+		cond_expr *conds = new cond_expr($1, GE_OP, $3);
+		PDEBUG("Matched: greater or equal set expr %s >= %s value %d\n", $1, $3, conds->eval());
+		$$ = conds;
+		free($1);
+		free($3);
+	}
+
+factor:	id_or_var TOK_LT id_or_var
+	{
+		cond_expr *conds = new cond_expr($1, LT_OP, $3);
+		PDEBUG("Matched: less set expr %s < %s value %d\n", $1, $3, conds->eval());
+		$$ = conds;
+		free($1);
+		free($3);
+	}
+
+factor:	id_or_var TOK_LE id_or_var
+	{
+		cond_expr *conds = new cond_expr($1, LE_OP, $3);
+		PDEBUG("Matched: less or equal set expr %s <= %s value %d\n", $1, $3, conds->eval());
+		$$ = conds;
+		free($1);
+		free($3);
+	}
+
 id_or_var: TOK_ID { $$ = $1; }
 id_or_var: TOK_SET_VAR { $$ = $1; };
 
diff --git a/parser/tst/Makefile b/parser/tst/Makefile
index 460cf6493..d36d9ff45 100644
--- a/parser/tst/Makefile
+++ b/parser/tst/Makefile
@@ -17,10 +17,10 @@ endif
 
 all: tests
 
-.PHONY: tests error_output gen_dbus gen_xtrans parser_sanity caching minimize equality dirtest valgrind
+.PHONY: tests error_output gen_dbus gen_xtrans parser_sanity caching minimize equality dirtest valgrind gen_conditionals gen_tests
 tests: error_output caching minimize equality dirtest parser_sanity
 
-GEN_TRANS_DIRS=simple_tests/generated_x/ simple_tests/generated_perms_leading/ simple_tests/generated_perms_safe/ simple_tests/generated_dbus
+GEN_TRANS_DIRS=simple_tests/generated_x/ simple_tests/generated_perms_leading/ simple_tests/generated_perms_safe/ simple_tests/generated_dbus simple_tests/generated_conditional/
 
 gen_xtrans: $(GEN_TRANS_DIRS)
 	./gen-xtrans.py
@@ -31,10 +31,15 @@ $(GEN_TRANS_DIRS):
 gen_dbus: $(GEN_TRANS_DIRS)
 	./gen-dbus.py
 
+gen_conditionals: $(GEN_TRANS_DIRS)
+	./gen-conditionals.py
+
+gen_tests: gen_xtrans gen_dbus gen_conditionals
+
 error_output: $(PARSER)
 	LANG=C ./errors.py -p "$(PARSER)" $(PYTEST_ARG)
 
-parser_sanity: $(PARSER) gen_xtrans gen_dbus
+parser_sanity: $(PARSER) gen_tests
 	$(Q)LANG=C APPARMOR_PARSER="$(PARSER)" ${PROVE} ${PROVE_ARG} ${TESTS}
 
 # use this target for faster manual testing if you don't want/need to test all the profiles generated by gen-*.py
@@ -54,7 +59,7 @@ equality: $(PARSER)
 dirtest: $(PARSER)
 	LANG=C APPARMOR_PARSER="$(PARSER) $(PARSER_ARGS)" ./dirtest.sh
 
-valgrind: $(PARSER) gen_xtrans gen_dbus
+valgrind: $(PARSER) gen_tests
 	LANG=C ./valgrind_simple.py -p "$(PARSER) $(PARSER_ARGS)" -v simple_tests
 
 $(PARSER):
diff --git a/parser/tst/gen-conditionals.py b/parser/tst/gen-conditionals.py
new file mode 100755
index 000000000..c8610ae9d
--- /dev/null
+++ b/parser/tst/gen-conditionals.py
@@ -0,0 +1,75 @@
+#!/usr/bin/python3
+#
+#   Copyright (c) 2025 Canonical, Ltd. (All rights reserved)
+#
+#   This program is free software; you can redistribute it and/or
+#   modify it under the terms of version 2 of the GNU General Public
+#   License published by the Free Software Foundation.
+#
+#   This program is distributed in the hope that it will be useful,
+#   but WITHOUT ANY WARRANTY; without even the implied warranty of
+#   MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+#   GNU General Public License for more details.
+#
+#   You should have received a copy of the GNU General Public License
+#   along with this program; if not, contact Canonical Ltd.
+#
+
+from testlib import write_file
+
+def gen_file(test, xres, op, lhs, rhs, add_else):
+    global count
+
+    content = ''
+    content += '#\n'
+    content += '#=DESCRIPTION {}\n'.format(test)
+    content += '#=EXRESULT {}\n'.format(xres)
+    content += '#\n'
+    if lhs['def'] and lhs != rhs:
+        content += '{} = {}\n'.format(lhs['varname'], lhs['def'])
+    if rhs['def']:
+        content += '{} = {}\n'.format(rhs['varname'], rhs['def'])
+    content += '/usr/bin/foo {\n'
+    content += '  if {} {} {} {{\n'.format(lhs['varname'], op, rhs['varname'])
+    content += '    /bin/true rix,\n'
+    content += '  }'
+    if add_else:
+        content += ' else {\n'
+        content += '    mount,\n'
+        content += '  }\n'
+    else:
+        content += '\n'
+
+    content += '}\n'
+
+    write_file('simple_tests/generated_conditional', '{}{}-{}.sd'.format(test, '-else' if add_else else '', count), content)
+
+    count += 1
+
+ops = {'==': 'equals', '!=': 'notequals', 'in': 'in', '>': 'greater', '>=': 'greaterequals', '<': 'lesser', '<=': 'lesserequals'}
+
+test_vars = [
+    {'varname': '@{VAR_EMPTY}', 'def': '""', 'desc': 'empty', 'number': False},  # empty var
+    {'varname': '@{VAR_ONE_STRING}', 'def': '/path/foo/', 'desc': 'var_one_string', 'number': False},  # one string in var
+    {'varname': '@{VAR_ONE_NUMBER}', 'def': '10', 'desc': 'var_one_number', 'number': True},  # one number in var
+    {'varname': '@{VAR_MULT_STRING}', 'def': '/path/foo/ /path/bar/', 'desc': 'var_mult_string', 'number': False},  # multiple strings in var
+    {'varname': '@{VAR_MULT_NUMBER}', 'def': '10 2 3.1', 'desc': 'var_mult_number', 'number': False},  # multiple numbers in var
+    {'varname': '@{VAR_MIXED}', 'def': '3 /foo 1 /bar/ 10 /path/foo/', 'desc': 'var_mixed', 'number': False},  # mixed var contents
+    {'varname': '10', 'def': '', 'desc': 'number1', 'number': True},  # number directly
+    {'varname': '9', 'def': '', 'desc': 'number2', 'number': True},  # number directly
+    {'varname': '/path/foo/', 'def': '', 'desc': 'string1', 'number': False},  # string directly
+    {'varname': '/path/baz/', 'def': '', 'desc': 'string2', 'number': False},  # string directly
+]
+
+def gen_files():
+    for op in ops:
+        for lhs in test_vars:
+            for rhs in test_vars:
+                for add_else in [True, False]:
+                    test_description = lhs['desc'] + '-' + ops[op]  + '-' + rhs['desc']
+                    xres = 'PASS' if lhs['number'] == rhs['number'] or op in ['in', '==', '!='] else 'FAIL'
+                    gen_file(test_description, xres, op, lhs, rhs, add_else)
+
+count = 0
+gen_files()
+print('Generated {} conditional tests'.format(count))
diff --git a/parser/tst/simple_tests/conditional/bad_4.sd b/parser/tst/simple_tests/conditional/bad_4.sd
new file mode 100644
index 000000000..f3e76e3eb
--- /dev/null
+++ b/parser/tst/simple_tests/conditional/bad_4.sd
@@ -0,0 +1,12 @@
+#=DESCRIPTION @FOO is not a boolean variable, but $FOO is defined
+#=EXRESULT FAIL
+
+$FOO=true
+$BAR=true
+$THREE=true
+
+/bin/true {
+  if not @FOO {
+      /bin/true rix,
+  }
+}
diff --git a/parser/tst/simple_tests/conditional/bad_5.sd b/parser/tst/simple_tests/conditional/bad_5.sd
new file mode 100644
index 000000000..91d5dcd9e
--- /dev/null
+++ b/parser/tst/simple_tests/conditional/bad_5.sd
@@ -0,0 +1,10 @@
+#=DESCRIPTION trying to use undefined boolean
+#=EXRESULT FAIL
+
+$FOO=true
+
+/bin/true {
+  if $BAR {
+    /bin/true rix,
+  }
+}
diff --git a/parser/tst/simple_tests/conditional/bad_6.sd b/parser/tst/simple_tests/conditional/bad_6.sd
new file mode 100644
index 000000000..21ee1acdf
--- /dev/null
+++ b/parser/tst/simple_tests/conditional/bad_6.sd
@@ -0,0 +1,9 @@
+#=DESCRIPTION unfinished else
+#=EXRESULT FAIL
+
+$BAR=true
+
+/bin/true {
+  if $BAR {
+    /bin/true rix,
+  } else {
diff --git a/parser/tst/simple_tests/conditional/bad_dup_hats_3.sd b/parser/tst/simple_tests/conditional/bad_dup_hats_3.sd
new file mode 100644
index 000000000..d4c4e5dc7
--- /dev/null
+++ b/parser/tst/simple_tests/conditional/bad_dup_hats_3.sd
@@ -0,0 +1,19 @@
+#=DESCRIPTION duplicated hats inside a conditional
+#=EXRESULT FAIL
+
+${FOO} = true
+
+/bin/true {
+
+  ^dupehat {
+    /bin/false rix,
+  }
+
+  if not ${FOO} {
+    /bin/true rm,
+  } else {
+    ^dupehat {
+      capability dac_override,
+    }
+  }
+}
diff --git a/parser/tst/simple_tests/conditional/ok_10.sd b/parser/tst/simple_tests/conditional/ok_10.sd
new file mode 100644
index 000000000..82cdf88bf
--- /dev/null
+++ b/parser/tst/simple_tests/conditional/ok_10.sd
@@ -0,0 +1,11 @@
+#=DESCRIPTION conditional within profile
+#=EXRESULT PASS
+
+$FOO=true
+$BAR=true
+
+/bin/true {
+  if $FOO and $BAR {
+      /bin/true rix,
+  }
+}
diff --git a/parser/tst/simple_tests/conditional/ok_11.sd b/parser/tst/simple_tests/conditional/ok_11.sd
new file mode 100644
index 000000000..aa544023b
--- /dev/null
+++ b/parser/tst/simple_tests/conditional/ok_11.sd
@@ -0,0 +1,11 @@
+#=DESCRIPTION conditional within profile
+#=EXRESULT PASS
+
+$FOO=true
+$BAR=true
+
+/bin/true {
+  if $FOO or $BAR {
+      /bin/true rix,
+  }
+}
diff --git a/parser/tst/simple_tests/conditional/ok_12.sd b/parser/tst/simple_tests/conditional/ok_12.sd
new file mode 100644
index 000000000..d51c32916
--- /dev/null
+++ b/parser/tst/simple_tests/conditional/ok_12.sd
@@ -0,0 +1,11 @@
+#=DESCRIPTION conditional within profile
+#=EXRESULT PASS
+
+$FOO=true
+$BAR=true
+
+/bin/true {
+  if ( $FOO and $BAR ) {
+      /bin/true rix,
+  }
+}
diff --git a/parser/tst/simple_tests/conditional/ok_13.sd b/parser/tst/simple_tests/conditional/ok_13.sd
new file mode 100644
index 000000000..989aa864d
--- /dev/null
+++ b/parser/tst/simple_tests/conditional/ok_13.sd
@@ -0,0 +1,12 @@
+#=DESCRIPTION conditional within profile
+#=EXRESULT PASS
+
+$FOO=true
+$BAR=true
+$THREE=true
+
+/bin/true {
+  if $FOO and $BAR and $THREE {
+      /bin/true rix,
+  }
+}
diff --git a/parser/tst/simple_tests/conditional/ok_14.sd b/parser/tst/simple_tests/conditional/ok_14.sd
new file mode 100644
index 000000000..1765ca1f0
--- /dev/null
+++ b/parser/tst/simple_tests/conditional/ok_14.sd
@@ -0,0 +1,12 @@
+#=DESCRIPTION conditional within profile
+#=EXRESULT PASS
+
+$FOO=true
+$BAR=true
+$THREE=true
+
+/bin/true {
+  if ($FOO and $BAR) and $THREE {
+      /bin/true rix,
+  }
+}
diff --git a/parser/tst/simple_tests/conditional/ok_15.sd b/parser/tst/simple_tests/conditional/ok_15.sd
new file mode 100644
index 000000000..65fba63ac
--- /dev/null
+++ b/parser/tst/simple_tests/conditional/ok_15.sd
@@ -0,0 +1,12 @@
+#=DESCRIPTION conditional within profile
+#=EXRESULT PASS
+
+$FOO=true
+$BAR=true
+$THREE=true
+
+/bin/true {
+  if $FOO and ($BAR and $THREE) {
+      /bin/true rix,
+  }
+}
diff --git a/parser/tst/simple_tests/conditional/ok_16.sd b/parser/tst/simple_tests/conditional/ok_16.sd
new file mode 100644
index 000000000..3d7e34c4d
--- /dev/null
+++ b/parser/tst/simple_tests/conditional/ok_16.sd
@@ -0,0 +1,12 @@
+#=DESCRIPTION conditional within profile
+#=EXRESULT PASS
+
+$FOO=true
+$BAR=true
+$THREE=true
+
+/bin/true {
+  if $FOO and (($BAR and $THREE)) {
+      /bin/true rix,
+  }
+}
diff --git a/parser/tst/simple_tests/conditional/ok_17.sd b/parser/tst/simple_tests/conditional/ok_17.sd
new file mode 100644
index 000000000..9a54b8aef
--- /dev/null
+++ b/parser/tst/simple_tests/conditional/ok_17.sd
@@ -0,0 +1,12 @@
+#=DESCRIPTION conditional within profile
+#=EXRESULT PASS
+
+$FOO=true
+$BAR=true
+$THREE=true
+
+/bin/true {
+  if ($FOO and (($BAR and $THREE))) {
+      /bin/true rix,
+  }
+}
diff --git a/parser/tst/simple_tests/conditional/ok_18.sd b/parser/tst/simple_tests/conditional/ok_18.sd
new file mode 100644
index 000000000..7387606e2
--- /dev/null
+++ b/parser/tst/simple_tests/conditional/ok_18.sd
@@ -0,0 +1,12 @@
+#=DESCRIPTION conditional within profile
+#=EXRESULT PASS
+
+$FOO=true
+$BAR=true
+$THREE=true
+
+/bin/true {
+  if ($FOO) and ($BAR or $THREE) {
+      /bin/true rix,
+  }
+}
diff --git a/parser/tst/simple_tests/conditional/ok_19.sd b/parser/tst/simple_tests/conditional/ok_19.sd
new file mode 100644
index 000000000..7425d145f
--- /dev/null
+++ b/parser/tst/simple_tests/conditional/ok_19.sd
@@ -0,0 +1,12 @@
+#=DESCRIPTION conditional within profile
+#=EXRESULT PASS
+
+$FOO=true
+$BAR=true
+$THREE=true
+
+/bin/true {
+  if ($FOO and $BAR) or $THREE {
+      /bin/true rix,
+  }
+}
diff --git a/parser/tst/simple_tests/conditional/ok_20.sd b/parser/tst/simple_tests/conditional/ok_20.sd
new file mode 100644
index 000000000..d3380dc67
--- /dev/null
+++ b/parser/tst/simple_tests/conditional/ok_20.sd
@@ -0,0 +1,12 @@
+#=DESCRIPTION conditional within profile
+#=EXRESULT PASS
+
+$FOO=true
+$BAR=true
+$THREE=true
+
+/bin/true {
+  if (($FOO and $BAR) or $THREE) {
+      /bin/true rix,
+  }
+}
diff --git a/parser/tst/simple_tests/conditional/ok_21.sd b/parser/tst/simple_tests/conditional/ok_21.sd
new file mode 100644
index 000000000..1bebcf590
--- /dev/null
+++ b/parser/tst/simple_tests/conditional/ok_21.sd
@@ -0,0 +1,12 @@
+#=DESCRIPTION conditional within profile
+#=EXRESULT PASS
+
+$FOO=true
+$BAR=true
+$THREE=true
+
+/bin/true {
+  if (($FOO and $BAR) or ($THREE)) {
+      /bin/true rix,
+  }
+}
diff --git a/parser/tst/simple_tests/conditional/ok_22.sd b/parser/tst/simple_tests/conditional/ok_22.sd
new file mode 100644
index 000000000..5f8cdbe81
--- /dev/null
+++ b/parser/tst/simple_tests/conditional/ok_22.sd
@@ -0,0 +1,12 @@
+#=DESCRIPTION conditional within profile
+#=EXRESULT PASS
+
+$FOO=true
+$BAR=true
+$THREE=true
+
+/bin/true {
+  if not $FOO and $BAR {
+      /bin/true rix,
+  }
+}
diff --git a/parser/tst/simple_tests/conditional/ok_23.sd b/parser/tst/simple_tests/conditional/ok_23.sd
new file mode 100644
index 000000000..6c758652d
--- /dev/null
+++ b/parser/tst/simple_tests/conditional/ok_23.sd
@@ -0,0 +1,12 @@
+#=DESCRIPTION conditional within profile
+#=EXRESULT PASS
+
+$FOO=true
+$BAR=true
+$THREE=true
+
+/bin/true {
+  if not $FOO and not $BAR {
+      /bin/true rix,
+  }
+}
diff --git a/parser/tst/simple_tests/conditional/ok_24.sd b/parser/tst/simple_tests/conditional/ok_24.sd
new file mode 100644
index 000000000..47e441f3f
--- /dev/null
+++ b/parser/tst/simple_tests/conditional/ok_24.sd
@@ -0,0 +1,12 @@
+#=DESCRIPTION conditional within profile
+#=EXRESULT PASS
+
+$FOO=true
+$BAR=true
+$THREE=true
+
+/bin/true {
+  if not not $FOO and not $BAR {
+      /bin/true rix,
+  }
+}
diff --git a/parser/tst/simple_tests/conditional/ok_25.sd b/parser/tst/simple_tests/conditional/ok_25.sd
new file mode 100644
index 000000000..cd150e592
--- /dev/null
+++ b/parser/tst/simple_tests/conditional/ok_25.sd
@@ -0,0 +1,12 @@
+#=DESCRIPTION conditional within profile
+#=EXRESULT PASS
+
+$FOO=true
+$BAR=true
+$THREE=true
+
+/bin/true {
+  if defined $FOO and $BAR {
+      /bin/true rix,
+  }
+}
diff --git a/parser/tst/simple_tests/conditional/ok_26.sd b/parser/tst/simple_tests/conditional/ok_26.sd
new file mode 100644
index 000000000..8d36de1aa
--- /dev/null
+++ b/parser/tst/simple_tests/conditional/ok_26.sd
@@ -0,0 +1,12 @@
+#=DESCRIPTION conditional within profile
+#=EXRESULT PASS
+
+$FOO=true
+$BAR=true
+$THREE=true
+
+/bin/true {
+  if defined $FOO and defined $BAR {
+      /bin/true rix,
+  }
+}
diff --git a/parser/tst/simple_tests/conditional/ok_27.sd b/parser/tst/simple_tests/conditional/ok_27.sd
new file mode 100644
index 000000000..1989b4738
--- /dev/null
+++ b/parser/tst/simple_tests/conditional/ok_27.sd
@@ -0,0 +1,12 @@
+#=DESCRIPTION conditional within profile
+#=EXRESULT PASS
+
+$FOO=true
+$BAR=true
+$THREE=true
+
+/bin/true {
+  if not defined $FOO and defined $BAR {
+      /bin/true rix,
+  }
+}
diff --git a/parser/tst/simple_tests/conditional/ok_28.sd b/parser/tst/simple_tests/conditional/ok_28.sd
new file mode 100644
index 000000000..f32500a47
--- /dev/null
+++ b/parser/tst/simple_tests/conditional/ok_28.sd
@@ -0,0 +1,12 @@
+#=DESCRIPTION conditional within profile
+#=EXRESULT PASS
+
+$FOO=true
+$BAR=true
+$THREE=true
+
+/bin/true {
+  if not defined $FOO and not defined $BAR {
+      /bin/true rix,
+  }
+}
diff --git a/parser/tst/simple_tests/conditional/ok_29.sd b/parser/tst/simple_tests/conditional/ok_29.sd
new file mode 100644
index 000000000..bdf19dd50
--- /dev/null
+++ b/parser/tst/simple_tests/conditional/ok_29.sd
@@ -0,0 +1,12 @@
+#=DESCRIPTION conditional within profile
+#=EXRESULT PASS
+
+$FOO=true
+$BAR=true
+$THREE=true
+
+/bin/true {
+  if not defined @FOO or not defined $BAR {
+      /bin/true rix,
+  }
+}
diff --git a/parser/tst/simple_tests/conditional/ok_30.sd b/parser/tst/simple_tests/conditional/ok_30.sd
new file mode 100644
index 000000000..b1f5576f7
--- /dev/null
+++ b/parser/tst/simple_tests/conditional/ok_30.sd
@@ -0,0 +1,11 @@
+#=DESCRIPTION conditional within profile
+#=EXRESULT PASS
+
+$FOO=true
+@{BAR}=10
+
+/bin/true {
+  if $FOO and @{BAR} >= 10 {
+      /bin/true rix,
+  }
+}
diff --git a/parser/tst/simple_tests/conditional/ok_31.sd b/parser/tst/simple_tests/conditional/ok_31.sd
new file mode 100644
index 000000000..678989e73
--- /dev/null
+++ b/parser/tst/simple_tests/conditional/ok_31.sd
@@ -0,0 +1,8 @@
+#=DESCRIPTION conditional within profile
+#=EXRESULT PASS
+
+/bin/true {
+  if defined $UNKNOWN {
+      /bin/true rix,
+  }
+}
diff --git a/parser/variable.cc b/parser/variable.cc
index c17d7e2c6..9c1860222 100644
--- a/parser/variable.cc
+++ b/parser/variable.cc
@@ -66,8 +66,6 @@ char *variable::process_var(const char *var)
 		orig++;
 		len--;
 	} else {
-		PERROR("ASSERT: Found var '%s' without variable prefix\n",
-		       var);
 		return NULL;
 	}
 
diff --git a/spread.yaml b/spread.yaml
index eeee192bc..2e27bd038 100644
--- a/spread.yaml
+++ b/spread.yaml
@@ -284,7 +284,7 @@ suites:
         summary: Unit tests for the Python utilities.
         prepare: |
             # Generate apparmor profiles that the tests rely on.
-            make -C "$SPREAD_PATH"/parser/tst gen_xtrans gen_dbus
+            make -C "$SPREAD_PATH"/parser/tst gen_tests
             # Spread does not support programmatically generated test variants.
             # Ensure that the list baked into utils/test/task.yaml contains all
             # the files matching utils/test/test-*.py
diff --git a/utils/apparmor/aa.py b/utils/apparmor/aa.py
index 9241692bb..22d0012b7 100644
--- a/utils/apparmor/aa.py
+++ b/utils/apparmor/aa.py
@@ -35,13 +35,14 @@ from apparmor.common import (
 from apparmor.profile_list import ProfileList, preamble_ruletypes
 from apparmor.profile_storage import ProfileStorage, add_or_remove_flag, ruletypes
 from apparmor.regex import (
-    RE_HAS_COMMENT_SPLIT, RE_PROFILE_CHANGE_HAT, RE_PROFILE_CONDITIONAL,
-    RE_PROFILE_CONDITIONAL_BOOLEAN, RE_PROFILE_CONDITIONAL_VARIABLE, RE_PROFILE_END,
+    RE_HAS_COMMENT_SPLIT, RE_PROFILE_CHANGE_HAT, RE_PROFILE_CONDITIONAL_START,
+    RE_PROFILE_CONDITIONAL_ELSE, RE_PROFILE_END,
     RE_PROFILE_HAT_DEF, RE_PROFILE_START, RE_METADATA_LOGPROF_SUGGEST,
     RE_RULE_HAS_COMMA, parse_profile_start_line, re_match_include)
 from apparmor.rule.abi import AbiRule
 from apparmor.rule.file import FileRule
 from apparmor.rule.include import IncludeRule
+from apparmor.rule.conditional import ConditionalBlock
 from apparmor.logparser import ReadLog
 from apparmor.translations import init_translation
 
@@ -1783,28 +1784,57 @@ def attach_profile_data(profiles, profile_data):
         profiles[p] = deepcopy(profile_data[p])
 
 
-def parse_profile_data(data, file, do_include, in_preamble):
+def parse_conditional(conditional_block, profile_data, data, lineno, file, do_include, in_preamble, profname, profile, debug_lineno):
+    cond_storage = ProfileStorage(profile_data[profname]['info']['profile'],
+                                  profile_data[profname]['info']['hat'],
+                                  profile_data[profname]['info']['calledby'] + ' in cond')
+    ret_lineno, ret_profile_data, end_of_block = parse_block(data[lineno + 1:], file, do_include, in_preamble, profname, profile, cond_storage, debug_lineno, in_if=True)
+    conditional_block.store_profile_data(ret_profile_data)
+    lineno = lineno + ret_lineno
+
+    if conditional_block.result:
+        for cond_profname in ret_profile_data:
+            if ret_profile_data[cond_profname]['in_cond']:
+                if profile_data.get(cond_profname, False):
+                    cond_prof_info = ret_profile_data[cond_profname].data['info']
+                    cond_prof_name = combine_name(cond_prof_info['profile'], cond_prof_info['hat'])
+                    raise AppArmorException(
+                        'Profile %(profile)s defined twice in %(file)s, last found in line %(line)s'
+                        % {'file': file, 'line': debug_lineno + 1, 'profile': cond_prof_name})
+                profile_data[cond_profname] = ret_profile_data[cond_profname]
+
+    if not end_of_block:
+        i = 1
+        if lineno + i < len(data):
+            next_line = data[lineno + i].strip()
+            matches = RE_PROFILE_CONDITIONAL_ELSE.search(next_line)
+            if matches and matches.group('close'):
+                data[lineno + i] = data[lineno + i].replace('}', '', 1)
+    else:
+        profile_data[profname]['cond_block'].add(conditional_block)
+        conditional_block = None
+
+    return lineno, conditional_block
+
+
+def parse_block(data, file, do_include, in_preamble, profname, profile, prof_storage, src_lineno, in_if=False):
     profile_data = {}
-    profile = None
     hat = None
-    profname = None
     in_contained_hat = None
     parsed_profiles = []
     initial_comment = ''
     lastline = None
+    conditional_block = None
 
-    active_profiles.init_file(file)
-
-    if do_include:
-        profile = file
-        hat = None
-        profname = combine_profname((profile, hat))
-        profile_data[profname] = ProfileStorage(profile, hat, 'parse_profile_data() do_include')
+    if do_include or profname and profname not in profile_data:
+        profile_data[profname] = prof_storage
         profile_data[profname]['filename'] = file
-
-    for lineno, line in enumerate(data):
-        line = line.strip()
+    lineno = 0
+    while lineno < len(data):
+        line = data[lineno].strip()
+        debug_lineno = src_lineno + lineno
         if not line:
+            lineno += 1
             continue
         # we're dealing with a multiline statement
         if lastline:
@@ -1812,11 +1842,13 @@ def parse_profile_data(data, file, do_include, in_preamble):
             lastline = None
 
         # is line handled by a *Rule class?
-        (rule_name, rule_obj) = match_line_against_rule_classes(line, profile, file, lineno, in_preamble)
+        (rule_name, rule_obj) = match_line_against_rule_classes(line, profile, file, debug_lineno, in_preamble)
         if rule_name:
             if in_preamble:
                 active_profiles.add_rule(file, rule_name, rule_obj)
             else:
+                if profname not in profile_data:
+                    profile_data[profname] = prof_storage
                 profile_data[profname][rule_name].add(rule_obj)
 
             if rule_name == 'inc_ie':
@@ -1838,16 +1870,16 @@ def parse_profile_data(data, file, do_include, in_preamble):
 
             in_preamble = False
 
-            (profile, hat, prof_storage) = ProfileStorage.parse(line, file, lineno, profile, hat)
-
+            (profile, hat, prof_storage) = ProfileStorage.parse(line, file, debug_lineno, profile, hat)
             if profile == hat:
                 hat = None
             profname = combine_profname((profile, hat))
 
             if profile_data.get(profname, False):
+                print(file)
                 raise AppArmorException(
                     'Profile %(profile)s defined twice in %(file)s, last found in line %(line)s'
-                    % {'file': file, 'line': lineno + 1, 'profile': combine_name(profile, hat)})
+                    % {'file': file, 'line': debug_lineno + 1, 'profile': combine_name(profile, hat)})
 
             profile_data[profname] = prof_storage
 
@@ -1857,12 +1889,11 @@ def parse_profile_data(data, file, do_include, in_preamble):
 
             initial_comment = ''
 
-        elif RE_PROFILE_END.search(line):
-            # If profile ends and we're not in one
-            if not profile:
-                raise AppArmorException(
-                    _('Syntax Error: Unexpected End of Profile reached in file: %(file)s line: %(line)s')
-                    % {'file': file, 'line': lineno + 1})
+            ret_lineno, ret_profile_data, end_of_block = parse_block(data[lineno + 1:], file, do_include, in_preamble, profname, profile, prof_storage, debug_lineno + 1, in_if)
+            profile_data[profname]['in_cond'] = in_if
+            lineno = lineno + ret_lineno
+
+            profile_data = {**profile_data, **ret_profile_data}
 
             if in_contained_hat:
                 hat = None
@@ -1876,32 +1907,49 @@ def parse_profile_data(data, file, do_include, in_preamble):
 
             initial_comment = ''
 
-        elif RE_PROFILE_CONDITIONAL.search(line):
-            # Conditional Boolean
-            pass
+        elif RE_PROFILE_END.search(line):
+            # If profile ends and we're not in one
+            if not profile:
+                raise AppArmorException(
+                    _('Syntax Error: Unexpected End of Profile reached in file: %(file)s line: %(line)s')
+                    % {'file': file, 'line': debug_lineno + 1})
 
-        elif RE_PROFILE_CONDITIONAL_VARIABLE.search(line):
-            # Conditional Variable defines
-            pass
+            return lineno + 1, profile_data, True
 
-        elif RE_PROFILE_CONDITIONAL_BOOLEAN.search(line):
-            # Conditional Boolean defined
-            pass
+        elif RE_PROFILE_CONDITIONAL_START.search(line):
+            conditional_block = ConditionalBlock(line, active_profiles.files[file])
+            lineno, conditional_block = parse_conditional(conditional_block, profile_data, data, lineno, file, do_include, in_preamble, profname, profile, debug_lineno + 1)
+
+        elif RE_PROFILE_CONDITIONAL_ELSE.search(line):
+            if not in_if and conditional_block is None:
+                raise AppArmorException(_('Syntax Error: Unexpected else without previous if in file: %(file)s line: %(line)s')
+                                        % {'file': file, 'line': debug_lineno + 1})
+
+            matches = RE_PROFILE_CONDITIONAL_ELSE.search(line)
+            if matches.group('close'):
+                return lineno, profile_data, False  # not returning next line on purpose
+
+            if conditional_block is None:
+                raise AppArmorException(_('Syntax Error: Unexpected else found without previous if in file: %(file)s line: %(line)s')
+                                        % {'file': file, 'line': debug_lineno + 1})
+            conditional_block.add_conditional(line, active_profiles.files[file])
+            lineno, conditional_block = parse_conditional(conditional_block, profile_data, data, lineno, file, do_include, in_preamble, profname, profile, debug_lineno + 1)
 
         elif RE_PROFILE_CHANGE_HAT.search(line):
             matches = RE_PROFILE_CHANGE_HAT.search(line).groups()
 
             if not profile:
                 raise AppArmorException(_('Syntax Error: Unexpected change hat declaration found in file: %(file)s line: %(line)s')
-                                        % {'file': file, 'line': lineno + 1})
+                                        % {'file': file, 'line': debug_lineno + 1})
 
             aaui.UI_Important(_('Ignoring no longer supported change hat declaration "^%(hat)s," found in file: %(file)s line: %(line)s')
-                              % {'hat': matches[0], 'file': file, 'line': lineno + 1})
+                              % {'hat': matches[0], 'file': file, 'line': debug_lineno + 1})
 
         elif line.startswith('#'):
             # Handle initial comments
             if not profile:
                 if line.startswith('# Last Modified:'):
+                    lineno += 1
                     continue
                 else:
                     initial_comment = initial_comment + line + '\n'
@@ -1925,14 +1973,16 @@ def parse_profile_data(data, file, do_include, in_preamble):
         else:
             raise AppArmorException(
                 _('Syntax Error: Unknown line found in file %(file)s line %(lineno)s:\n    %(line)s')
-                % {'file': file, 'lineno': lineno + 1, 'line': line})
+                % {'file': file, 'lineno': debug_lineno, 'line': line})
+
+        lineno += 1
 
     if lastline:
         # lastline gets merged into line (and reset to None) when reading the next line.
         # If it isn't empty, this means there's something unparsable at the end of the profile
         raise AppArmorException(
             _('Syntax Error: Unknown line found in file %(file)s line %(lineno)s:\n    %(line)s')
-            % {'file': file, 'lineno': lineno + 1, 'line': lastline})
+            % {'file': file, 'lineno': debug_lineno + 1, 'line': lastline})
 
     # Below is not required I'd say
     if not do_include:
@@ -1952,6 +2002,30 @@ def parse_profile_data(data, file, do_include, in_preamble):
             _("Syntax Error: Missing '}' or ','. Reached end of file %(file)s while inside profile %(profile)s")
             % {'file': file, 'profile': profile})
 
+    return lineno, profile_data, False
+
+
+def parse_profile_data(data, file, do_include, in_preamble):
+    profile_data = {}
+    profile = None
+    hat = None
+    profname = None
+    prof_storage = None
+
+    active_profiles.init_file(file)
+
+    if do_include:
+        profile = file
+        hat = None
+        profname = combine_profname((profile, hat))
+        prof_storage = ProfileStorage(profile, hat, 'parse_profile_data() do_include')
+
+    _lineno, profile_data, end_of_block = parse_block(data, file, do_include, in_preamble, profname, profile, prof_storage, 0)
+
+    for prof in list(profile_data):  # get the keys
+        if profile_data[prof]['in_cond']:
+            profile_data.pop(prof)
+
     return profile_data
 
 
diff --git a/utils/apparmor/profile_storage.py b/utils/apparmor/profile_storage.py
index e35d1c565..a357cbc9d 100644
--- a/utils/apparmor/profile_storage.py
+++ b/utils/apparmor/profile_storage.py
@@ -35,6 +35,7 @@ from apparmor.rule.io_uring import IOUringRule, IOUringRuleset
 from apparmor.rule.mount import MountRule, MountRuleset
 from apparmor.rule.pivot_root import PivotRootRule, PivotRootRuleset
 from apparmor.rule.unix import UnixRule, UnixRuleset
+from apparmor.rule.conditional import ConditionalBlock, ConditionalBlockset
 
 from apparmor.translations import init_translation
 
@@ -58,6 +59,7 @@ ruletypes = {
     'mount':          {'rule': MountRule,         'ruleset': MountRuleset},
     'pivot_root':     {'rule': PivotRootRule,     'ruleset': PivotRootRuleset},
     'unix':           {'rule': UnixRule,          'ruleset': UnixRuleset},
+    'cond_block':     {'rule': ConditionalBlock,  'ruleset': ConditionalBlockset},
 }
 
 
@@ -88,6 +90,7 @@ class ProfileStorage:
         data['profile_keyword'] = False
         data['is_hat'] = False  # profile or hat?
         data['hat_keyword'] = False  # True for 'hat foo', False for '^foo'
+        data['in_cond'] = False  # used for profiles created inside conditionals
 
         self.data = data
 
@@ -178,6 +181,7 @@ class ProfileStorage:
             'inc_ie',
             'rlimit',
             'capability',
+            'cond_block',
             'network',
             'dbus',
             'mount',
diff --git a/utils/apparmor/regex.py b/utils/apparmor/regex.py
index a7a93ea22..d1e53b8c4 100644
--- a/utils/apparmor/regex.py
+++ b/utils/apparmor/regex.py
@@ -28,7 +28,7 @@ RE_COMMA_EOL = r'\s*,' + RE_EOL  # optional whitespace, comma + RE_EOL
 
 RE_PROFILE_NAME = r'(?P<%s>(\S+|"[^"]+"))'  # string without spaces, or quoted string. %s is the match group name
 RE_PATH = r'/\S*|"/[^"]*"'  # filename (starting with '/') without spaces, or quoted filename.
-RE_VAR = r'@{[^}\s]+}'
+RE_VAR = r'@{?[^}\s]+}?'
 RE_DICT_ENTRY = r'\s*(?P<key>[^,\s=]+)(?:=(?P<value>[^,\s=]+))?\s*'
 RE_PROFILE_PATH = '(?P<%s>(' + RE_PATH + '))'  # quoted or unquoted filename. %s is the match group name
 RE_PROFILE_PATH_OR_VAR = '(?P<%s>(' + RE_PATH + '|' + RE_VAR + r'\S*|"' + RE_VAR + '[^"]*"))'  # quoted or unquoted filename or variable. %s is the match group name
@@ -37,6 +37,10 @@ RE_XATTRS = r'(\s+xattrs\s*=\s*\((?P<xattrs>([^)=]+(=[^)=]+)?\s?)*)\)\s*)?'
 RE_FLAGS = r'(\s+(flags\s*=\s*)?\((?P<flags>[^)]+)\))?'
 
 RE_VARIABLE = re.compile(RE_VAR)
+RE_ID = r'(?P<id%(label)s>[^,!#\s=@$()"]+|"(\w|\s)*")'
+RE_VARIABLES = r'(?P<var%(label)s>(?P<var_type%(label)s>@|\$)\{?(?P<varname%(label)s>\w+)\}?)'
+RE_ID_OR_VAR = r'(' + RE_VARIABLES + r'|' + RE_ID + r')'
+RE_ALL_VARIABLES = re.compile(RE_VARIABLES % {'label': ''})
 
 RE_PROFILE_END = re.compile(r'^\s*\}' + RE_EOL)
 RE_PROFILE_ALL = re.compile(RE_PRIORITY_AUDIT_DENY + r'all' + RE_COMMA_EOL)
@@ -45,9 +49,21 @@ RE_PROFILE_ALIAS = re.compile(r'^\s*alias\s+(?P<orig_path>"??.+?"??)\s+->\s*(?P<
 RE_PROFILE_RLIMIT = re.compile(r'^\s*set\s+rlimit\s+(?P<rlimit>[a-z]+)\s*<=\s*(?P<value>[^ ]+(\s+[a-zA-Z]+)?)' + RE_COMMA_EOL)
 RE_PROFILE_BOOLEAN = re.compile(r'^\s*(?P<varname>\$\{?\w*\}?)\s*=\s*(?P<value>true|false)\s*,?' + RE_EOL, flags=re.IGNORECASE)
 RE_PROFILE_VARIABLE = re.compile(r'^\s*(?P<varname>@\{?\w+\}?)\s*(?P<mode>\+?=)\s*(?P<values>@*.+?)' + RE_EOL)
-RE_PROFILE_CONDITIONAL = re.compile(r'^\s*if\s+(not\s+)?(\$\{?\w*\}?)\s*\{' + RE_EOL)
-RE_PROFILE_CONDITIONAL_VARIABLE = re.compile(r'^\s*if\s+(not\s+)?defined\s+(@\{?\w+\}?)\s*\{\s*(#.*)?$')
-RE_PROFILE_CONDITIONAL_BOOLEAN = re.compile(r'^\s*if\s+(not\s+)?defined\s+(\$\{?\w+\}?)\s*\{\s*(#.*)?$')
+
+RE_BOOLEAN_OP = r'(?P<boolean_op%(term)s>(?P<boolean_not%(term)s>(not\s+)*)(?P<defined%(term)s>defined\s+)?' + RE_VARIABLES % {'label': '%(term)s'} + r')'
+RE_COMPARE_OP_QUOTED = r'(?P<compare_op%(term)s>(?P<compare_not%(term)s>(not\s+)*)(?P<left%(term)s>"?' + RE_ID_OR_VAR % {'label': '_left%(term)s'} + r'"?)\s+(?P<op%(term)s>==|!=|in|>|>=|<|<=)\s+(?P<right%(term)s>"?' + RE_ID_OR_VAR % {'label': '_right%(term)s'} + r'"?))'  # used only by transform_cond
+RE_COMPARE_OP = RE_COMPARE_OP_QUOTED.replace('"?', '')
+
+RE_FACTOR = r'(?P<open_paren%(term)s>\()?(' + RE_COMPARE_OP + r'|' + RE_BOOLEAN_OP + r')(?P<close_paren%(term)s>\))?'
+
+RE_TERM = r'(?P<open_paren%(expr)s>\()*\s*((?P<one%(expr)s>' + RE_FACTOR % {'term': '_1%(expr)s'} + r')\s+(?P<cond_op%(expr)s>and|or)\s+(?P<two%(expr)s>' + RE_FACTOR % {'term': '_2%(expr)s'} + ')|' + RE_FACTOR % {'term': '_0%(expr)s'} + r')\s*(?P<close_paren%(expr)s>\))*'
+
+RE_CONDITION = r'(?P<expr>(?P<open_paren>\()?(?P<first>' + RE_TERM % {'expr': '_first'} + r')(\s+(?P<cond_op>and|or)\s+(?P<second>' + RE_TERM % {'expr': '_second'} + r'))*(?P<close_paren>\))?)'
+
+RE_PROFILE_CONDITIONAL = r'\s*if\s+' + RE_CONDITION + r'\s*\{'
+
+RE_PROFILE_CONDITIONAL_START = re.compile(r'^' + RE_PROFILE_CONDITIONAL + RE_EOL)
+RE_PROFILE_CONDITIONAL_ELSE = re.compile(r'^\s*(?P<close>\})?\s*else((?P<if>\s+' + RE_PROFILE_CONDITIONAL + r')|(\s*\{))' + RE_EOL)
 RE_PROFILE_NETWORK = re.compile(RE_PRIORITY_AUDIT_DENY + r'network(?P<details>\s+.*)?' + RE_COMMA_EOL)
 RE_PROFILE_CHANGE_HAT = re.compile(r'^\s*\^("??.+?"??)' + RE_COMMA_EOL)
 RE_PROFILE_HAT_DEF = re.compile(r'^(?P<leadingspace>\s*)(?P<hat_keyword>\^|hat\s+)(?P<hat>"??[^)]+?"??)' + RE_FLAGS + r'\s*\{' + RE_EOL)
diff --git a/utils/apparmor/rule/boolean.py b/utils/apparmor/rule/boolean.py
index ec1b901e8..b3364a083 100644
--- a/utils/apparmor/rule/boolean.py
+++ b/utils/apparmor/rule/boolean.py
@@ -51,7 +51,7 @@ class BooleanRule(BaseRule):
             raise AppArmorException('Passed invalid value to %s: %s' % (self.__class__.__name__, value))
 
         self.varname = varname
-        self.value = value
+        self.value = value == 'true'
 
     @classmethod
     def _create_instance(cls, raw_rule, matches):
@@ -70,7 +70,7 @@ class BooleanRule(BaseRule):
 
         space = '  ' * depth
 
-        return '%s%s = %s' % (space, self.varname, self.value)
+        return '%s%s = %s' % (space, self.varname, str(self.value).lower())
 
     def _is_covered_localvars(self, other_rule):
         """check if other_rule is covered by this rule object"""
@@ -78,7 +78,10 @@ class BooleanRule(BaseRule):
         if self.varname != other_rule.varname:
             return False
 
-        if not self._is_covered_list(self.value, None, set(other_rule.value), None, 'value'):
+        if type(self.value) is not bool or type(other_rule.value) is not bool:
+            raise AppArmorBug(_('Invalid value for boolean variable'))
+
+        if self.value != other_rule.value:
             return False
 
         # still here? -> then it is covered
diff --git a/utils/apparmor/rule/conditional.py b/utils/apparmor/rule/conditional.py
new file mode 100644
index 000000000..dd3f97361
--- /dev/null
+++ b/utils/apparmor/rule/conditional.py
@@ -0,0 +1,534 @@
+#
+# ----------------------------------------------------------------------
+#    Copyright (C) 2025 Canonical, Ltd.
+#
+#    This program is free software; you can redistribute it and/or
+#    modify it under the terms of version 2 of the GNU General Public
+#    License as published by the Free Software Foundation.
+#
+#    This program is distributed in the hope that it will be useful,
+#    but WITHOUT ANY WARRANTY; without even the implied warranty of
+#    MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+#    GNU General Public License for more details.
+#
+# ----------------------------------------------------------------------
+
+import ast
+import re
+
+from apparmor.common import AppArmorException, AppArmorBug
+from apparmor.regex import strip_quotes, RE_PROFILE_CONDITIONAL_START, RE_PROFILE_CONDITIONAL_ELSE, RE_ALL_VARIABLES, RE_BOOLEAN_OP, RE_ID_OR_VAR, RE_CONDITION, RE_COMPARE_OP_QUOTED
+from apparmor.rule import BaseRule, BaseRuleset, parse_comment, quote_if_needed
+from apparmor.translations import init_translation
+
+_ = init_translation()
+
+
+class ConditionalBlock(BaseRule):
+    """Class to handle and store a conditional block containing if,
+    and optionally, else ifs and else"""
+
+    _match_re = None
+    result = False
+
+    def __init__(self, raw_rule, prof_storage, audit=False, deny=False, allow_keyword=False,
+                 comment='', log_event=None, priority=None):
+
+        super().__init__(audit=audit, deny=deny, allow_keyword=allow_keyword,
+                         comment=comment, log_event=log_event, priority=priority)
+
+        # conditional blocks don't support priority, allow keyword, audit or deny - yet
+        self.ensure_modifiers_not_supported()
+
+        self.cond_list = []
+        conditional = ConditionalStart.create_instance(raw_rule)
+        self.result = conditional.evaluate(prof_storage)
+        self.cond_list.append(conditional)
+
+    def store_profile_data(self, profile_data):
+        self.cond_list[-1].profile_data = profile_data
+
+    def add_conditional(self, raw_rule, prof_storage):
+        conditional = ConditionalElse.create_instance(raw_rule)
+        result = conditional.evaluate(prof_storage)
+        self.cond_list.append(conditional)
+        if self.result:
+            self.result = False
+        else:
+            self.result = result
+
+    def get_clean(self, depth=0):
+        clean = ''
+        for cond in self.cond_list:
+            if clean:
+                clean += ' '
+            clean += cond.get_clean(depth)
+        return clean
+
+    @classmethod
+    def _create_instance(cls, raw_rule, matches):
+        raise NotImplementedError("'%s' is not supposed to be called directly" % (str(cls)))
+
+    def _is_covered_localvars(self, other_rule):
+        """check if other_rule is covered by this rule object"""
+        if len(self.cond_list) != len(other_rule.cond_list):
+            return False
+        else:
+            for idx in range(len(self.cond_list)):
+                if not self.cond_list[idx].is_covered(other_rule.cond_list[idx]):
+                    return False
+        return True
+
+    def _is_equal_localvars(self, other_rule, strict):
+        """compare if rule-specific conditionals are equal"""
+        if len(self.cond_list) != len(other_rule.cond_list):
+            return False
+        else:
+            for idx in range(len(self.cond_list)):
+                if not self.cond_list[idx].is_equal(other_rule.cond_list[idx]):
+                    return False
+        return True
+
+    def _logprof_header_localvars(self):
+        conditions = []
+        for cond in self.cond_list:
+            conditions.append(cond.logprof_header())
+        return _('ConditionalBlock'), (conditions)
+
+
+class ConditionalRule(BaseRule):
+    """Class to handle and store a single conditional rule"""
+
+    IF = 1
+    ELSEIF = 2
+    ELSE = 3
+    rule_name = 'conditional'
+    _match_re = re.compile(RE_CONDITION)
+
+    def __init__(self, condition, ast_tree,
+                 audit=False, deny=False, allow_keyword=False,
+                 comment='', log_event=None, priority=None):
+
+        super().__init__(audit=audit, deny=deny, allow_keyword=allow_keyword,
+                         comment=comment, log_event=log_event, priority=priority)
+
+        # conditionals don't support priority, allow keyword, audit or deny
+        self.ensure_modifiers_not_supported()
+
+        if condition not in [self.IF, self.ELSEIF, self.ELSE]:
+            raise AppArmorBug('Passed invalid condition to %s: %s' % (self.__class__.__name__, condition))
+        if ast_tree is not None and not isinstance(ast_tree, AppArmorAst):
+            raise AppArmorBug('Passed invalid AST tree type to %s: %s' % (self.__class__.__name__, type(ast_tree)))
+
+        self.condition = condition
+        self.ast_tree = ast_tree
+
+    @classmethod
+    def _create_instance(cls, raw_rule, matches):
+        """parse raw_rule and return instance of this class"""
+
+        if cls == ConditionalStart:
+            conditional = ConditionalRule.IF
+        else:
+            if matches.group('if'):
+                conditional = ConditionalRule.ELSEIF
+            else:
+                conditional = ConditionalRule.ELSE
+
+        comment = parse_comment(matches)
+
+        expr = cls._match_re.search(raw_rule)
+        ast_tree = None
+        if conditional != ConditionalRule.ELSE:
+            ast_tree = AppArmorAst(expr.group('expr'))
+
+        return cls(conditional, ast_tree, comment)
+
+    def evaluate(self, prof_storage):
+        # else should always evaluate to true, since that's the
+        # default if all previous "ifs" evaluated to false
+        if self.condition == ConditionalRule.ELSE:
+            return True
+
+        return self.ast_tree.evaluate(prof_storage)
+
+    def get_clean(self, depth=0):
+        """return rule (in clean/default formatting)"""
+
+        space = '  ' * depth
+        leading_space = ''
+        if self.condition == ConditionalRule.IF:
+            conditional = 'if '
+            leading_space = space
+        elif self.condition == ConditionalRule.ELSEIF:
+            conditional = 'else if '
+        elif self.condition == ConditionalRule.ELSE:
+            conditional = 'else '
+        else:
+            raise AppArmorBug('Invalid condition type in %s' % (self.__class__.__name__))
+
+        expr = ''
+        if self.ast_tree:
+            expr = self.ast_tree.get_clean()
+
+        data = []
+        data.append('%s%s%s{' % (leading_space, conditional, expr))
+
+        for profname in self.profile_data:
+            if self.profile_data[profname]['in_cond']:
+                from apparmor.aa import write_piece
+                data.extend(write_piece(self.profile_data, depth + 1, profname, profname))
+            else:
+                data += self.profile_data[profname].get_rules_clean(depth + 1)
+
+        data.append('%s}' % space)
+        return '\n'.join(data)
+
+    def _is_covered_localvars(self, other_rule):
+        """check if other_rule is covered by this rule object"""
+        # conditional is only covered if equal
+        if self.is_equal(other_rule):
+            return True
+        return False
+
+    def _is_equal_localvars(self, rule_obj, strict):
+        """compare if rule-specific conditionals are equal"""
+        if self.condition != rule_obj.condition:
+            return False
+        if self.profile_data != rule_obj.profile_data:
+            return False
+        return self.ast_tree.is_equal(rule_obj.ast_tree)
+
+    def _logprof_header_localvars(self):
+        return _('Conditional'), self.get_clean()
+
+
+class ConditionalStart(ConditionalRule):
+    """Class to handle and store a single conditional rule"""
+
+    _match_re = RE_PROFILE_CONDITIONAL_START
+
+
+class ConditionalElse(ConditionalRule):
+    """Class to handle and store a single conditional rule"""
+
+    _match_re = RE_PROFILE_CONDITIONAL_ELSE
+
+
+class ConditionalBlockset(BaseRuleset):
+    """Class to handle and store a collection of conditional rule blocks"""
+
+
+class AppArmorAst():
+    astcomp_to_string = {
+        ast.Eq: '==',
+        ast.NotEq: '!=',
+        ast.Lt: '<',
+        ast.LtE: '<=',
+        ast.Gt: '>',
+        ast.GtE: '>=',
+        ast.In: 'in',
+    }
+
+    def __init__(self, expr):
+        self.tree = ast.parse(self.transform_cond(expr))
+
+    def get_clean(self):
+        noop, expr = self.get_clean_tree(self.tree.body[0])
+        expr += ' '
+        return expr
+
+    def get_clean_tree(self, node):
+        if isinstance(node, ast.Expr):
+            node = node.value
+        if isinstance(node, ast.BoolOp):
+            op = ''
+            clean = ''
+            if isinstance(node.op, ast.And):
+                op = 'and'
+            else:
+                op = 'or'
+            for value in node.values:
+                if clean:
+                    clean += ' ' + op + ' '
+                ret_op, ret_clean = self.get_clean_tree(value)
+                if ret_op == 'or' and op == 'and':
+                    ret_clean = '(' + ret_clean + ')'
+                clean += ret_clean
+            return op, clean
+        elif isinstance(node, ast.UnaryOp):
+            if not isinstance(node.op, ast.Not):
+                raise AppArmorBug('Invalid unary operation in %s' % (self.__class__.__name__))
+            op, child = self.get_clean_tree(node.operand)
+            if op == 'not':  # remove canceling nots
+                return 'val', '%s' % (child[len('not '):])
+            return 'not', 'not %s' % (child)
+        elif isinstance(node, ast.Constant):
+            val = quote_if_needed(strip_quotes(node.value))  # strip first because it might it can be quoted but not need it
+            term = Term.create_instance(val)
+            return 'val', str(term)
+        elif isinstance(node, ast.Name):
+            return 'func', node.id
+        elif isinstance(node, ast.Call):
+            noop, name = self.get_clean_tree(node.func)
+            if name != 'defined':
+                raise AppArmorBug('Invalid function name in %s' % (self.__class__.__name__))
+            noop, var = self.get_clean_tree(node.args[0])
+            return 'defined', '%s %s' % (name, var)
+        elif isinstance(node, ast.Compare):
+            noop, left = self.get_clean_tree(node.left)
+            noop, right = self.get_clean_tree(node.comparators[0])
+            op = self.astcomp_to_string[type(node.ops[0])]
+            return 'cmp', '%s %s %s' % (left, op, right)
+        else:
+            raise AppArmorBug('Unsupported node type in %s' % (self.__class__.__name__))
+
+    def evaluate(self, prof_storage):
+        noop, result = self.evaluate_tree(self.tree.body[0], prof_storage, True)
+        return result
+
+    def evaluate_tree(self, node, prof_storage, resolve=False):
+        result = None
+        if isinstance(node, ast.Expr):
+            node = node.value
+        if isinstance(node, ast.BoolOp):
+            op = node.op
+            for value in node.values:
+                ret_op, ret_result = self.evaluate_tree(value, prof_storage, True)
+                if result is None:
+                    result = ret_result
+                else:
+                    if isinstance(op, ast.And):
+                        result = result and ret_result
+                    else:
+                        result = result or ret_result
+            return op, result
+        elif isinstance(node, ast.UnaryOp):
+            if not isinstance(node.op, ast.Not):
+                raise AppArmorBug('Invalid unary operation in %s' % (self.__class__.__name__))
+            result = not self.evaluate_tree(node.operand, prof_storage, True)
+            return node.op, result
+        elif isinstance(node, ast.Constant):
+            val = quote_if_needed(strip_quotes(node.value))  # strip first because it might it can be quoted but not need it
+            term = Term.create_instance(val)
+            if resolve:
+                cond = BooleanCondition('', term)
+                result = cond.evaluate(prof_storage)
+            return term, result
+        elif isinstance(node, ast.Name):
+            return node.id, result
+        elif isinstance(node, ast.Call):
+            func, noop = self.evaluate_tree(node.func, prof_storage)
+            if func != 'defined':
+                raise AppArmorBug('Invalid function name in %s' % (self.__class__.__name__))
+            # there should be only one arg
+            variable, noop = self.evaluate_tree(node.args[0], prof_storage)
+            cond = BooleanCondition(func, variable)
+            return 'defined', cond.evaluate(prof_storage)
+        elif isinstance(node, ast.Compare):
+            left, noop = self.evaluate_tree(node.left, prof_storage)
+            right, noop = self.evaluate_tree(node.comparators[0], prof_storage)
+            op = self.astcomp_to_string[type(node.ops[0])]
+            cond = CompareCondition(left, op, right)
+            return 'cmp', cond.evaluate(prof_storage)
+        else:
+            raise AppArmorBug('Unsupported node type in %s' % (self.__class__.__name__))
+
+    def compare_ast(self, node1, node2):
+        if type(node1) is not type(node2):
+            return False
+        if isinstance(node1, ast.AST):
+            for k, v in vars(node1).items():
+                if k in ('lineno', 'col_offset', 'ctx', 'end_lineno', 'end_col_offset'):
+                    continue
+                if not self.compare_ast(v, getattr(node2, k)):
+                    return False
+            return True
+        elif isinstance(node1, list):
+            if len(node1) != len(node2):
+                return False
+            for i in range(len(node1)):
+                if not self.compare_ast(node1[i], node2[i]):
+                    return False
+            return True
+        else:
+            return node1 == node2
+
+    def is_equal(self, other_tree):
+        return self.compare_ast(self.tree, other_tree.tree)
+
+    def transform_cond(self, text):
+        """Used to transform policy conditional into Python format, so ast can be used"""
+
+        def boolean_op(match):
+            not_op = match.group('boolean_not')
+            defined = match.group('defined')
+            var = match.group('var')
+            var = '"%s"' % (var)
+            if defined:
+                var = 'defined(%s)' % (var)
+            return '%s%s' % (not_op, var)
+
+        def compare_op(match):
+            not_op = match.group('compare_not')
+            left = match.group('left')
+            op = match.group('op')
+            right = match.group('right')
+
+            if match.group('id_left') and not (left.startswith('"') or left.endswith('"')):
+                left = '"%s"' % (left)
+            if match.group('id_right') and not (right.startswith('"') or right.endswith('"')):
+                right = '"%s"' % (right)
+
+            return '%s%s %s %s' % (not_op, left, op, right)
+
+        replaced = re.sub(RE_BOOLEAN_OP % {'term': ''}, boolean_op, text)
+        replaced = re.sub(RE_COMPARE_OP_QUOTED % {'term': ''}, compare_op, replaced)
+        return replaced
+
+
+class Term():
+    match_re = re.compile(RE_ID_OR_VAR % {'label': ''})
+
+    @classmethod
+    def create_instance(cls, raw_term):
+        """parse raw_term and return instance of this class"""
+        matches = cls.match_re.search(raw_term)
+        if not matches:
+            raise AppArmorBug('Unable to parse term in %s' % (cls.__class__.__name__))
+        if matches.group('id'):
+            return Id(matches.group('id'))
+        else:
+            var_type = matches.group('var_type')
+            varname = matches.group('varname')
+            var = matches.group('var')
+            return Variable(var_type, varname, var)
+
+
+class Variable(Term):
+    def __init__(self, var_type, varname, var):
+        self.varname = varname
+        self.var = var
+        if var_type == '$':
+            self.var_type = 'boolean'
+        else:
+            self.var_type = 'variable'
+
+    def get_variable_rule(self, prof_storage):
+        for rule in prof_storage[self.var_type].rules:
+            filtered = RE_ALL_VARIABLES.search(rule.varname)
+            if self.varname == filtered.group('varname'):
+                return rule
+        return None
+
+    def get_set(self, prof_storage):
+        variable_rule = self.get_variable_rule(prof_storage)
+        if variable_rule is None:
+            raise AppArmorException(_('Error retrieving variable %(var)s') % {'var': self.var})
+        return variable_rule.values
+
+    def __repr__(self):
+        return self.var
+
+
+class Id(Term):
+    def __init__(self, value):
+        self.value = value
+
+    def get_set(self, prof_storage):
+        return {self.value}
+
+    def __repr__(self):
+        return self.value
+
+
+class BooleanCondition():
+    def __init__(self, defined: str, variable: Term):
+        if not isinstance(defined, str):
+            raise AppArmorBug('Passed invalid defined value to %s: %s' % (self.__class__.__name__, defined))
+        if not isinstance(variable, Term):
+            raise AppArmorBug('Passed invalid variable type to %s: %s' % (self.__class__.__name__, type(variable)))
+
+        self.defined = defined
+        self.variable = variable
+
+    def evaluate(self, prof_storage):
+        matched = self.variable.get_variable_rule(prof_storage)
+
+        if not self.defined:  # boolean op
+            if self.variable.var_type == 'boolean':
+                if matched:
+                    return matched.value
+                else:
+                    raise AppArmorException(_('Cannot find previous declaration of %(var)s') % {'var': self.variable})
+            else:
+                raise AppArmorException(_('Unexpected variable in boolean operation: %(var)s') % {'var': self.variable})
+        else:
+            return bool(matched)
+
+
+class CompareCondition():
+    valid_ops = ['==', '!=', 'in', '>', '>=', '<', '<=']
+
+    def __init__(self, left_term: Term, op: str, right_term: Term):
+        if op not in self.valid_ops:
+            raise AppArmorBug('Passed invalid op value to %s: %s' % (self.__class__.__name__, op))
+        if not isinstance(left_term, Term):
+            raise AppArmorBug('Passed invalid left term type to %s: %s' % (self.__class__.__name__, type(left_term)))
+        if not isinstance(right_term, Term):
+            raise AppArmorBug('Passed invalid right term type to %s: %s' % (self.__class__.__name__, type(right_term)))
+
+        self.left_term = left_term
+        self.op = op
+        self.right_term = right_term
+
+    def compare(self, op, lhs, rhs):
+        if type(lhs) is not type(rhs):
+            raise AppArmorBug('Trying to compare elements of different types in %s' % (self.__class__.__name__))
+
+        if (op == '>'):
+            return lhs > rhs
+        elif (op == '>='):
+            return lhs >= rhs
+        elif (op == '<'):
+            return lhs < rhs
+        elif (op == '<='):
+            return lhs <= rhs
+        else:
+            raise AppArmorBug('Invalid op in %s: %s' % (self.__class__.__name__, op))
+
+    def evaluate(self, prof_storage):
+        lhs = self.left_term.get_set(prof_storage)
+        rhs = self.right_term.get_set(prof_storage)
+
+        if not isinstance(lhs, set) or not isinstance(rhs, set):
+            raise AppArmorBug('Passed invalid type for condition term in %s' % (self.__class__.__name__))
+
+        converted_lhs = None
+        converted_rhs = None
+
+        if self.op == 'in':
+            return lhs.issubset(rhs)
+        elif self.op == '==':
+            return lhs == rhs
+        elif self.op == '!=':
+            return lhs != rhs
+
+        try:
+            if len(lhs) == 1:
+                converted_lhs = int(next(iter(lhs)))
+        except ValueError:
+            pass
+
+        try:
+            if len(rhs) == 1:
+                converted_rhs = int(next(iter(rhs)))
+        except ValueError:
+            pass
+
+        if converted_lhs is None and converted_rhs is None:  # sets
+            return self.compare(self.op, lhs, rhs)
+        elif converted_lhs is not None and converted_rhs is not None:  # numbers
+            return self.compare(self.op, converted_lhs, converted_rhs)
+        else:
+            raise AppArmorException(_('Can only compare numbers with numbers'))
diff --git a/utils/apparmor/rule/variable.py b/utils/apparmor/rule/variable.py
index a88fc42de..ee4865ade 100644
--- a/utils/apparmor/rule/variable.py
+++ b/utils/apparmor/rule/variable.py
@@ -40,10 +40,10 @@ class VariableRule(BaseRule):
 
         if not isinstance(varname, str):
             raise AppArmorBug('Passed unknown type for varname to %s: %s' % (self.__class__.__name__, varname))
-        if not varname.startswith('@{'):
-            raise AppArmorException("Passed invalid varname to %s (doesn't start with '@{'): %s" % (self.__class__.__name__, varname))
-        if not varname.endswith('}'):
-            raise AppArmorException("Passed invalid varname to %s (doesn't end with '}'): %s" % (self.__class__.__name__, varname))
+        if not varname.startswith('@'):
+            raise AppArmorException("Passed invalid varname to %s (doesn't start with '@'): %s" % (self.__class__.__name__, varname))
+        if (varname.startswith('@{') and not varname.endswith('}')) or (not varname.startswith('@{') and varname.endswith('}')):
+            raise AppArmorException("Passed invalid varname to %s (mismatched braces): %s" % (self.__class__.__name__, varname))
 
         if not isinstance(mode, str):
             raise AppArmorBug('Passed unknown type for variable assignment mode to %s: %s' % (self.__class__.__name__, mode))
diff --git a/utils/test/cleanprof_test.complain b/utils/test/cleanprof_test.complain
index 1ad59d756..cdcf525af 100644
--- a/utils/test/cleanprof_test.complain
+++ b/utils/test/cleanprof_test.complain
@@ -107,3 +107,20 @@ profile foo//bar {
 /usr/bin/a/simple/cleanprof/test/profile//child {
        /home/test-child r,
           }
+
+profile uniquename /attach {
+    if not not
+    not not
+    not not defined $foo {
+          /bin/true rix,
+    }       else if x in @xy {
+      if   @{asdf}  >   " a test"  {
+            /greaterthan r,
+      } else {
+  file,
+      }
+      /bin/false rix,
+    }    else        {
+           /dev/null r,
+         }
+}
diff --git a/utils/test/cleanprof_test.in b/utils/test/cleanprof_test.in
index e9f13299c..8c8624c45 100644
--- a/utils/test/cleanprof_test.in
+++ b/utils/test/cleanprof_test.in
@@ -107,3 +107,20 @@ profile foo//bar {
 /usr/bin/a/simple/cleanprof/test/profile//child {
        /home/test-child r,
           }
+
+profile uniquename /attach {
+    if not not
+    not not
+    not not defined $foo {
+          /bin/true rix,
+    }       else if x in @xy {
+      if   @{asdf}  >   " a test"  {
+            /greaterthan r,
+      } else {
+  file,
+      }
+      /bin/false rix,
+    }    else        {
+           /dev/null r,
+         }
+}
diff --git a/utils/test/cleanprof_test.out b/utils/test/cleanprof_test.out
index aa501b1b1..441e606c1 100644
--- a/utils/test/cleanprof_test.out
+++ b/utils/test/cleanprof_test.out
@@ -86,3 +86,24 @@ profile foo//bar {
   /home/namedchild r,
 
 }
+profile uniquename /attach {
+  if defined $foo {
+    /bin/true rix,
+
+  } else if x in @xy {
+    if @{asdf} > " a test" {
+      /greaterthan r,
+
+    } else {
+      file,
+
+    }
+
+    /bin/false rix,
+
+  } else {
+    /dev/null r,
+
+  }
+
+}
diff --git a/utils/test/test-boolean.py b/utils/test/test-boolean.py
index cc588e3f9..1cbab26a7 100644
--- a/utils/test/test-boolean.py
+++ b/utils/test/test-boolean.py
@@ -44,12 +44,12 @@ class BooleanTest(AATest):
 class BooleanTestParse(BooleanTest):
     tests = (
         # rawrule                                   comment    varname  value
-        ('$foo=true',                        exp('',           '$foo',  'true')),
-        ('$foo = false',                     exp('',           '$foo',  'false')),
-        ('$foo=TrUe',                        exp('',           '$foo',  'true')),
-        ('$foo = FaLsE',                     exp('',           '$foo',  'false')),
-        ('  $foo =   true   ',               exp('',           '$foo',  'true')),
-        ('  $foo =   true        # comment', exp(' # comment', '$foo',  'true')),
+        ('$foo=true',                        exp('',           '$foo',  True)),
+        ('$foo = false',                     exp('',           '$foo',  False)),
+        ('$foo=TrUe',                        exp('',           '$foo',  True)),
+        ('$foo = FaLsE',                     exp('',           '$foo',  False)),
+        ('  $foo =   true   ',               exp('',           '$foo',  True)),
+        ('  $foo =   true        # comment', exp(' # comment', '$foo',  True)),
     )
 
     def _run_test(self, rawrule, expected):
diff --git a/utils/test/test-conditional.py b/utils/test/test-conditional.py
new file mode 100644
index 000000000..e7eea5715
--- /dev/null
+++ b/utils/test/test-conditional.py
@@ -0,0 +1,402 @@
+#!/usr/bin/python3
+# ----------------------------------------------------------------------
+#    Copyright (C) 2025 Canonical, Ltd.
+#
+#    This program is free software; you can redistribute it and/or
+#    modify it under the terms of version 2 of the GNU General Public
+#    License as published by the Free Software Foundation.
+#
+#    This program is distributed in the hope that it will be useful,
+#    but WITHOUT ANY WARRANTY; without even the implied warranty of
+#    MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+#    GNU General Public License for more details.
+#
+# ----------------------------------------------------------------------
+
+import unittest
+
+from apparmor.common import AppArmorException, AppArmorBug, combine_profname
+from apparmor.profile_storage import ProfileStorage
+from apparmor.profile_list import ProfileList
+from apparmor.rule.file import FileRule
+from apparmor.rule.variable import VariableRule
+from apparmor.rule.boolean import BooleanRule
+from apparmor.rule.conditional import ConditionalBlock, AppArmorAst, Term, CompareCondition, ConditionalRule, BooleanCondition
+from common_test import AATest, setup_all_loops
+
+
+class TestConditional(AATest):
+    """ Base class to test conditionals, profile_data does not contain any rules """
+    filename = 'somefile'
+    condition_contents = '\n'
+
+    tests = (
+        # ConditionalBlock                                                        clean rule
+        (['if $FOO {', '} else if $BAR {', '} else {'],                           'if $FOO {' + condition_contents + '} else if $BAR {' + condition_contents + '} else {' + condition_contents + '}'),
+        (['if not $FOO {', '} else if not $BAR {', '} else {'],                   'if not $FOO {' + condition_contents + '} else if not $BAR {' + condition_contents + '} else {' + condition_contents + '}'),
+        (['if defined $FOO {', '} else if not defined $BAR {', '} else {'],       'if defined $FOO {' + condition_contents + '} else if not defined $BAR {' + condition_contents + '} else {' + condition_contents + '}'),
+        (['if not defined @{VAR2} {', '} else if defined @{VAR1} {', '} else {'], 'if not defined @{VAR2} {' + condition_contents + '} else if defined @{VAR1} {' + condition_contents + '} else {' + condition_contents + '}'),
+        (['if not defined @{VAR2} {', '} else {'],                                'if not defined @{VAR2} {' + condition_contents + '} else {' + condition_contents + '}'),
+        (['if not defined @{VAR2} {'],                                            'if not defined @{VAR2} {' + condition_contents + '}'),
+    )
+
+    @classmethod
+    def setUpClass(cls):
+        super(TestConditional, cls).setUpClass()
+        cls.active_profiles = ProfileList()
+        cls.profile_data = {}
+        cls.condition_contents = '\n'
+        (profile, hat, prof_storage) = ProfileStorage.parse('profile foo {', cls.filename, 0, False, False)
+        cls.profile_data[profile] = prof_storage
+        cls.active_profiles.add_rule(cls.filename, 'variable', VariableRule.create_instance('@{VAR1} = "test"'))
+        cls.active_profiles.add_rule(cls.filename, 'variable', VariableRule.create_instance('@{VAR2} = "test1 test2"'))
+        cls.active_profiles.add_rule(cls.filename, 'variable', VariableRule.create_instance('@{VAR3} = 10'))
+        cls.active_profiles.add_rule(cls.filename, 'boolean', BooleanRule.create_instance('$FOO=true'))
+        cls.active_profiles.add_rule(cls.filename, 'boolean', BooleanRule.create_instance('$BAR=false'))
+
+    def _run_test(self, params, expected):
+        conditional_block = None
+        for condition in params:
+            if condition == params[0]:
+                conditional_block = ConditionalBlock(condition, self.active_profiles.files[self.filename])
+                conditional_block.store_profile_data(self.profile_data)
+            else:
+                conditional_block.add_conditional(condition, self.active_profiles.files[self.filename])
+                conditional_block.store_profile_data(self.profile_data)
+
+        self.assertEqual(conditional_block.get_clean(), expected)
+
+
+class TestConditionalComplex(TestConditional):
+    """ Class to test complex conditionals (and, ors, comparisons and boolean operations), profile_data contains one file rule """
+    # directly related to how setUpClass sets up profile_data
+    condition_contents = '\n  /bin/false rix,\n\n'
+
+    tests = (
+        # ConditionalBlock                                                            clean rule
+        (['if $FOO and ($BAR) {', '} else if $BAR {', '} else {'],                    'if $FOO and $BAR {' + condition_contents + '} else if $BAR {' + condition_contents + '} else {' + condition_contents + '}'),
+        (['if $FOO and ($BAR or defined @{VAR1}) {', '} else if $BAR {', '} else {'], 'if $FOO and ($BAR or defined @{VAR1}) {' + condition_contents + '} else if $BAR {' + condition_contents + '} else {' + condition_contents + '}'),
+        (['if $FOO or ($BAR or defined @{VAR1}) {', '} else if $BAR {', '} else {'],  'if $FOO or $BAR or defined @{VAR1} {' + condition_contents + '} else if $BAR {' + condition_contents + '} else {' + condition_contents + '}'),
+        (['if $FOO or ($BAR and defined @{VAR1}) {', '} else if $BAR {', '} else {'], 'if $FOO or $BAR and defined @{VAR1} {' + condition_contents + '} else if $BAR {' + condition_contents + '} else {' + condition_contents + '}'),
+        (['if not $FOO {', '} else if not not $BAR {', '} else {'],                   'if not $FOO {' + condition_contents + '} else if $BAR {' + condition_contents + '} else {' + condition_contents + '}'),
+        (['if ((test in @{VAR1})) and defined $FOO {'],                               'if test in @{VAR1} and defined $FOO {' + condition_contents + '}'),
+        (['if test3 in @{VAR2} {'],                                                   'if test3 in @{VAR2} {' + condition_contents + '}'),
+        (['if 9 < @{VAR3} {'],                                                        'if 9 < @{VAR3} {' + condition_contents + '}'),
+        (['if test in "test2 test" {'],                                               'if test in "test2 test" {' + condition_contents + '}'),
+    )
+
+    @classmethod
+    def setUpClass(cls):
+        super(TestConditionalComplex, cls).setUpClass()
+        (profile, hat, prof_storage) = ProfileStorage.parse('profile foo {', cls.filename, 0, False, False)
+        cls.profile_data[profile] = prof_storage
+        cls.profile_data[profile]['file'].add(FileRule.create_instance('/bin/false rix,'))
+
+
+class TestConditionalSimple(TestConditional):
+    """ Class to test simple conditionals (boolean and defined operations), profile_data contains one file rule """
+    # directly related to how setUpClass sets up profile_data
+    condition_contents = '\n  /bin/false rix,\n\n'
+
+    tests = (
+        # ConditionalBlock                                                        clean rule
+        (['if $FOO {', '} else if $BAR {', '} else {'],                           'if $FOO {' + condition_contents + '} else if $BAR {' + condition_contents + '} else {' + condition_contents + '}'),
+        (['if not $FOO {', '} else if not $BAR {', '} else {'],                   'if not $FOO {' + condition_contents + '} else if not $BAR {' + condition_contents + '} else {' + condition_contents + '}'),
+        (['if defined $FOO {', '} else if not defined ${BAR} {', '} else {'],     'if defined $FOO {' + condition_contents + '} else if not defined ${BAR} {' + condition_contents + '} else {' + condition_contents + '}'),
+        (['if not defined @{VAR2} {', '} else if defined @{VAR1} {', '} else {'], 'if not defined @{VAR2} {' + condition_contents + '} else if defined @{VAR1} {' + condition_contents + '} else {' + condition_contents + '}'),
+        (['if not defined @{VAR2} {', '} else {'],                                'if not defined @{VAR2} {' + condition_contents + '} else {' + condition_contents + '}'),
+        (['if not defined @{VAR2} {'],                                            'if not defined @{VAR2} {' + condition_contents + '}'),
+    )
+
+    @classmethod
+    def setUpClass(cls):
+        super(TestConditionalSimple, cls).setUpClass()
+        (profile, hat, prof_storage) = ProfileStorage.parse('profile foo {', cls.filename, 0, False, False)
+        cls.profile_data[profile] = prof_storage
+        cls.profile_data[profile]['file'].add(FileRule.create_instance('/bin/false rix,'))
+
+
+class TestConditionalSubProfile(TestConditional):
+    """ Class to test simple conditionals, profile_data contains hat definition """
+    # directly related to how setUpClass sets up profile_data
+    condition_contents = '\n  /** w,\n  /bin/false rix,\n\n  ^bar {\n    /bin/true rix,\n\n  }\n'
+
+    tests = (
+        # ConditionalBlock                                                        clean rule
+        (['if $FOO {', '} else if $BAR {', '} else {'],                           'if $FOO {' + condition_contents + '} else if $BAR {' + condition_contents + '} else {' + condition_contents + '}'),
+        (['if not $FOO {', '} else if not $BAR {', '} else {'],                   'if not $FOO {' + condition_contents + '} else if not $BAR {' + condition_contents + '} else {' + condition_contents + '}'),
+        (['if defined $FOO {', '} else if not defined ${BAR} {', '} else {'],     'if defined $FOO {' + condition_contents + '} else if not defined ${BAR} {' + condition_contents + '} else {' + condition_contents + '}'),
+        (['if not defined @{VAR2} {', '} else if defined @{VAR1} {', '} else {'], 'if not defined @{VAR2} {' + condition_contents + '} else if defined @{VAR1} {' + condition_contents + '} else {' + condition_contents + '}'),
+        (['if not defined @{VAR2} {', '} else {'],                                'if not defined @{VAR2} {' + condition_contents + '} else {' + condition_contents + '}'),
+        (['if not defined @{VAR2} {'],                                            'if not defined @{VAR2} {' + condition_contents + '}'),
+    )
+
+    @classmethod
+    def setUpClass(cls):
+        super(TestConditionalSubProfile, cls).setUpClass()
+        (profile, hat, prof_storage) = ProfileStorage.parse('profile foo {', cls.filename, 0, False, False)
+        cls.profile_data[profile] = prof_storage
+        cls.profile_data[profile]['file'].add(FileRule.create_instance('/bin/false rix,'))
+        cls.profile_data[profile]['file'].add(FileRule.create_instance('/** w,'))
+        (profile, hat, prof_storage) = ProfileStorage.parse('^bar {', cls.filename, 0, profile, None)
+        profname = combine_profname((profile, hat))
+        cls.profile_data[profname] = prof_storage
+        cls.profile_data[profname]['in_cond'] = True
+        cls.profile_data[profname]['file'].add(FileRule.create_instance('/bin/true rix,'))
+
+
+class TestConditionalLogprof(TestConditional):
+    """ Class to test output of Logprof """
+    # directly related to how setUpClass sets up profile_data
+    condition_contents = '\n  /** w,\n  /bin/false rix,\n\n  ^bar {\n    /bin/true rix,\n\n  }\n'
+
+    tests = (
+        (['if $FOO {', '} else if $BAR {', '} else {'],
+         ['ConditionalBlock', [['Conditional', 'if $FOO {' + condition_contents + '}'],
+                               ['Conditional', 'else if $BAR {' + condition_contents + '}'],
+                               ['Conditional', 'else {' + condition_contents + '}']]]),
+        (['if not $FOO {', '} else if not $BAR {', '} else {'],
+         ['ConditionalBlock', [['Conditional', 'if not $FOO {' + condition_contents + '}'],
+                               ['Conditional', 'else if not $BAR {' + condition_contents + '}'],
+                               ['Conditional', 'else {' + condition_contents + '}']]]),
+        (['if defined $FOO {', '} else if not defined $BAR {', '} else {'],
+         ['ConditionalBlock', [['Conditional', 'if defined $FOO {' + condition_contents + '}'],
+                               ['Conditional', 'else if not defined $BAR {' + condition_contents + '}'],
+                               ['Conditional', 'else {' + condition_contents + '}']]]),
+        (['if not defined @{VAR2} {', '} else if defined @{VAR1} {', '} else {'],
+         ['ConditionalBlock', [['Conditional', 'if not defined @{VAR2} {' + condition_contents + '}'],
+                               ['Conditional', 'else if defined @{VAR1} {' + condition_contents + '}'],
+                               ['Conditional', 'else {' + condition_contents + '}']]]),
+        (['if not defined @{VAR2} {', '} else {'],
+         ['ConditionalBlock', [['Conditional', 'if not defined @{VAR2} {' + condition_contents + '}'],
+                               ['Conditional', 'else {' + condition_contents + '}']]]),
+        (['if not defined @{VAR2} {'],
+         ['ConditionalBlock', [['Conditional', 'if not defined @{VAR2} {' + condition_contents + '}']]]),
+    )
+
+    @classmethod
+    def setUpClass(cls):
+        super(TestConditionalLogprof, cls).setUpClass()
+        (profile, hat, prof_storage) = ProfileStorage.parse('profile foo {', cls.filename, 0, False, False)
+        cls.profile_data[profile] = prof_storage
+        cls.profile_data[profile]['file'].add(FileRule.create_instance('/bin/false rix,'))
+        cls.profile_data[profile]['file'].add(FileRule.create_instance('/** w,'))
+        (profile, hat, prof_storage) = ProfileStorage.parse('^bar {', cls.filename, 0, profile, None)
+        profname = combine_profname((profile, hat))
+        cls.profile_data[profname] = prof_storage
+        cls.profile_data[profname]['in_cond'] = True
+        cls.profile_data[profname]['file'].add(FileRule.create_instance('/bin/true rix,'))
+
+    def _run_test(self, params, expected):
+        conditional_block = None
+        for condition in params:
+            if condition == params[0]:
+                conditional_block = ConditionalBlock(condition, self.active_profiles.files[self.filename])
+                conditional_block.store_profile_data(self.profile_data)
+            else:
+                conditional_block.add_conditional(condition, self.active_profiles.files[self.filename])
+                conditional_block.store_profile_data(self.profile_data)
+
+        self.assertEqual(conditional_block.logprof_header(), expected)
+
+
+class TestConditionalEquality(AATest):
+    """ Class to test equality tests """
+    filename = 'somefile'
+    profile_data = {}
+
+    tests = (
+        # should always be different
+        # first condition                                   second condition
+        ((['if not $FOO {'], profile_data),                 (['if $FOO {'], profile_data)),
+        ((['if defined $FOO {'], profile_data),             (['if $FOO {'], profile_data)),
+        ((['if $BAR {'], profile_data),                     (['if $FOO {'], profile_data)),
+        ((['if $FOO {'], None),                             (['if $FOO {'], profile_data)),
+        ((['if $FOO {', '} else if $BAR {'], profile_data), (['if $FOO {', '} else {'], profile_data)),
+        ((['if $FOO and $BAR {'], profile_data),            (['if $FOO and $BAR and defined $BAZ{'], profile_data)),
+    )
+
+    @classmethod
+    def setUpClass(cls):
+        super(TestConditionalEquality, cls).setUpClass()
+        cls.active_profiles = ProfileList()
+        (profile, hat, prof_storage) = ProfileStorage.parse('profile foo {', cls.filename, 0, False, False)
+        cls.profile_data[profile] = prof_storage
+        cls.profile_data[profile]['file'].add(FileRule.create_instance('/bin/false rix,'))
+        cls.profile_data[profile]['file'].add(FileRule.create_instance('/** w,'))
+        (profile, hat, prof_storage) = ProfileStorage.parse('^bar {', cls.filename, 0, profile, None)
+        profname = combine_profname((profile, hat))
+        cls.profile_data[profname] = prof_storage
+        cls.profile_data[profname]['in_cond'] = True
+        cls.profile_data[profname]['file'].add(FileRule.create_instance('/bin/true rix,'))
+        cls.active_profiles.add_rule(cls.filename, 'variable', VariableRule.create_instance('@{VAR1} = "test"'))
+        cls.active_profiles.add_rule(cls.filename, 'boolean', BooleanRule.create_instance('$FOO=true'))
+        cls.active_profiles.add_rule(cls.filename, 'boolean', BooleanRule.create_instance('$BAR=false'))
+
+    def init_cond(self, conds, profile_data):
+        block = None
+        for cond in conds:
+            if cond == conds[0]:
+                block = ConditionalBlock(cond, self.active_profiles.files[self.filename])
+                block.store_profile_data(profile_data)
+            else:
+                block.add_conditional(cond, self.active_profiles.files[self.filename])
+                block.store_profile_data(profile_data)
+        return block
+
+    def _run_test(self, cond1, cond2):
+        conditional_block1 = self.init_cond(cond1[0], cond1[1])
+        conditional_block2 = self.init_cond(cond2[0], cond2[1])
+
+        self.assertFalse(conditional_block1.is_equal(conditional_block2))
+        self.assertFalse(conditional_block1.is_covered(conditional_block2))
+
+    def test_is_equal_condition(self):
+        conditional_block1 = self.init_cond(['if $FOO {', '} else if $BAR {', '} else {'], self.profile_data)
+        conditional_block2 = self.init_cond(['if $FOO {', '} else {'], self.profile_data)
+
+        self.assertFalse(conditional_block1.is_equal(conditional_block2))
+        self.assertFalse(conditional_block1.is_covered(conditional_block2))
+
+    def test_is_equal(self):
+        conditional_block1 = ConditionalBlock('if not defined $FOO {', self.active_profiles.files[self.filename])
+        conditional_block1.store_profile_data(self.profile_data)
+
+        self.assertTrue(conditional_block1.is_equal(conditional_block1))
+        self.assertTrue(conditional_block1.is_covered(conditional_block1))
+
+
+class TestConditionalException(AATest):
+    filename = 'somefile'
+    profile_data = {}
+
+    tests = (
+        (['if @{VAR1} {', '} else if $BAR {', '} else {'], AppArmorException),  # set variable used in boolean comparison
+        (['if $FOO {', '} else if @{VAR} {', '} else {'],  AppArmorException),  # undefined variable in else if
+        (['if ${BAZ} {', '} else {'],                      AppArmorException),  # undefined boolean variable with else
+        (['if ${VAR} {'],                                  AppArmorException),  # undefined boolean variable
+        (['if foo in @{UNDERFINED} {'],                    AppArmorException),  # undefined set variable
+    )
+
+    @classmethod
+    def setUpClass(cls):
+        super(TestConditionalException, cls).setUpClass()
+        cls.active_profiles = ProfileList()
+        cls.condition_contents = '\n'
+        (profile, hat, prof_storage) = ProfileStorage.parse('profile foo {', cls.filename, 0, False, False)
+        cls.profile_data[profile] = prof_storage
+        cls.active_profiles.add_rule(cls.filename, 'variable', VariableRule.create_instance('@{VAR1} = "test"'))
+        cls.active_profiles.add_rule(cls.filename, 'boolean', BooleanRule.create_instance('$FOO=true'))
+        cls.active_profiles.add_rule(cls.filename, 'boolean', BooleanRule.create_instance('$BAR=false'))
+
+    def _run_test(self, params, expected):
+        conditional_block = None
+        with self.assertRaises(expected):
+            for condition in params:
+                if condition == params[0]:
+                    conditional_block = ConditionalBlock(condition, self.active_profiles.files[self.filename])
+                    conditional_block.store_profile_data(self.profile_data)
+                else:
+                    conditional_block.add_conditional(condition, self.active_profiles.files[self.filename])
+                    conditional_block.store_profile_data(self.profile_data)
+
+    def test_create_instance_block1(self):
+        with self.assertRaises(NotImplementedError):
+            ConditionalBlock.create_instance('test')
+
+    def test_create_instance_block2(self):
+        with self.assertRaises(NotImplementedError):
+            ConditionalBlock._create_instance('test', None)
+
+
+class TestAppArmorAstException(AATest):
+    tests = (
+        ('foo = "1"',    AppArmorBug),  # AppArmorAst only supports the actual condition
+        ('~ $FOO',       AppArmorBug),  # Invalid unary operator
+        ('func(${BAZ})', AppArmorBug),  # Invalid function name
+    )
+
+    def _run_test(self, params, expected):
+        ast = AppArmorAst(params)
+        with self.assertRaises(expected):
+            ast.get_clean()
+        with self.assertRaises(expected):
+            ast.evaluate(None)
+
+
+class TestMiscClassException(AATest):
+    def test_invalid_op_1(self):
+        term = Term.create_instance('10')
+        op = 'is'
+        with self.assertRaises(AppArmorBug):
+            CompareCondition(term, op, term)
+
+    def test_invalid_op_2(self):
+        term = Term.create_instance('10')
+        cond = CompareCondition(term, 'in', term)
+        cond.op = 'is'
+        with self.assertRaises(AppArmorBug):
+            cond.evaluate(None)
+
+    def test_invalid_term(self):
+        with self.assertRaises(AppArmorBug):
+            Term.create_instance('#')
+
+    def test_invalid_conditional_condition(self):
+        with self.assertRaises(AppArmorBug):
+            ConditionalRule('invalid', AppArmorAst('defined $BAR'))
+
+    def test_invalid_conditional_ast_tree(self):
+        with self.assertRaises(AppArmorBug):
+            ConditionalRule(ConditionalRule.IF, 'defined $BAR')
+
+    def test_invalid_conditional_clean(self):
+        cond = ConditionalRule(ConditionalRule.IF, AppArmorAst('defined $BAR'))
+        cond.condition = 'invalid'
+        with self.assertRaises(AppArmorBug):
+            cond.get_clean()
+
+    def test_invalid_boolean_defined(self):
+        with self.assertRaises(AppArmorBug):
+            BooleanCondition(None, Term.create_instance('10'))
+
+    def test_invalid_boolean_varible(self):
+        with self.assertRaises(AppArmorBug):
+            BooleanCondition('defined', '10')
+
+    def test_invalid_compare_left(self):
+        with self.assertRaises(AppArmorBug):
+            CompareCondition(None, '==', Term.create_instance('10'))
+
+    def test_invalid_compare_right(self):
+        with self.assertRaises(AppArmorBug):
+            CompareCondition(Term.create_instance('10'), '==', None)
+
+    def test_invalid_compare_op(self):
+        with self.assertRaises(AppArmorBug):
+            CompareCondition(Term.create_instance('10'), '~', Term.create_instance('10'))
+
+    def test_invalid_compare(self):
+        term = Term.create_instance('10')
+        cond = CompareCondition(term, '==', term)
+        with self.assertRaises(AppArmorBug):
+            cond.compare(cond.op, term.get_set(None), 10)
+
+    def test_invalid_compare_evaluate(self):
+        term = InvalidTerm(10)
+        cond = CompareCondition(term, '==', term)
+        with self.assertRaises(AppArmorBug):
+            cond.evaluate(None)
+
+
+class InvalidTerm(Term):
+    def __init__(self, value):
+        self.value = value
+
+    def get_set(self, prof_storage):
+        return self.value  # not a set
+
+
+setup_all_loops(__name__)
+if __name__ == '__main__':
+    unittest.main(verbosity=1)
diff --git a/utils/test/test-parser-simple-tests.py b/utils/test/test-parser-simple-tests.py
index 833dd8e43..fbba878f4 100644
--- a/utils/test/test-parser-simple-tests.py
+++ b/utils/test/test-parser-simple-tests.py
@@ -340,27 +340,6 @@ syntax_failure = (
     # missing profile keywords
     'profile/re_named_ok2.sd',
 
-    # Syntax Errors caused by boolean conditions (parse_profile_data() gets confused by the closing '}')
-    'conditional/defined_1.sd',
-    'conditional/defined_2.sd',
-    'conditional/else_1.sd',
-    'conditional/else_2.sd',
-    'conditional/else_3.sd',
-    'conditional/else_if_1.sd',
-    'conditional/else_if_2.sd',
-    'conditional/else_if_3.sd',
-    'conditional/else_if_5.sd',
-    'conditional/ok_1.sd',
-    'conditional/ok_2.sd',
-    'conditional/ok_3.sd',
-    'conditional/ok_4.sd',
-    'conditional/ok_5.sd',
-    'conditional/ok_6.sd',
-    'conditional/ok_7.sd',
-    'conditional/ok_8.sd',
-    'conditional/ok_9.sd',
-    'conditional/stress_1.sd',
-
     # unexpected uppercase vs. lowercase in *x rules
     'file/ok_5.sd',  # Invalid mode UX
     'file/ok_2.sd',  # Invalid mode RWM