diff --git a/src/error.c b/src/error.c
index 9bb3be8a04..13541697f2 100644
--- a/src/error.c
+++ b/src/error.c
@@ -583,6 +583,19 @@ void CheckSameLength(const Char * desc, const Char *leftName, const Char *rightN
     }
 }
 
+/****************************************************************************
+**
+*F  Warning
+*/
+void Warning(const Char * msg, Int arg1, Int arg2)
+{
+    Pr("Warning, ", 0, 0);
+    Pr(msg, arg1, arg2);
+    if (strcmp("*stdin*", GetInputFilename()) != 0)
+        Pr(" in %s:%d", (Int)GetInputFilename(), GetInputLineNumber());
+    Pr("\n", 0, 0);
+}
+
 /****************************************************************************
 **
 *V  GVarFuncs . . . . . . . . . . . . . . . . . . list of functions to export
diff --git a/src/error.h b/src/error.h
index 31af2564b4..1a8439f392 100644
--- a/src/error.h
+++ b/src/error.h
@@ -148,6 +148,13 @@ void CheckIsDenseList(const Char * desc, const Char * listName, Obj list);
 void CheckSameLength(const Char * desc, const Char *leftName, const Char *rightName, Obj left, Obj right);
 
 
+/****************************************************************************
+**
+*F  Warning
+*/
+extern void Warning(const Char * msg, Int arg1, Int arg2);
+
+
 /****************************************************************************
 **
 *F * * * * * * * * * * * * * * initialize module * * * * * * * * * * * * * *
diff --git a/src/exprs.c b/src/exprs.c
index 56deffafaa..265568e814 100644
--- a/src/exprs.c
+++ b/src/exprs.c
@@ -183,15 +183,27 @@ Obj             EvalAnd (
     }
 
     /* handle the 'and' of two filters                                    */
-    else if ( TNUM_OBJ(opL) == T_FUNCTION ) {
+    else if (IS_PSEUDO_FILTER(opL)) {
+        if (!IS_FILTER(opL)) {
+            // support this for backwards compatibility; see discussion on
+            // https://github.com/gap-system/gap/pull/2732
+            Warning("operation '%g' used in AND-filter is not a filter",
+                    (Int)NAME_FUNC(opL), 0);
+        }
         tmp = READ_EXPR(expr, 1);
         opR = EVAL_EXPR( tmp );
-        if ( TNUM_OBJ(opR) == T_FUNCTION ) {
+        if (IS_PSEUDO_FILTER(opR)) {
+            if (!IS_FILTER(opR)) {
+                // support this for backwards compatibility; see discussion on
+                // https://github.com/gap-system/gap/pull/2732
+                Warning("operation '%g' used in AND-filter is not a filter",
+                        (Int)NAME_FUNC(opR), 0);
+            }
             return NewAndFilter( opL, opR );
         }
         else {
             ErrorQuit(
-                "<expr> must be 'true' or 'false' (not a %s)",
+                "<expr> must be a filter (not a %s)",
                 (Int)TNAM_OBJ(opL), 0L );
         }
     }
@@ -199,7 +211,7 @@ Obj             EvalAnd (
     /* signal an error                                                     */
     else {
         ErrorQuit(
-            "<expr> must be 'true' or 'false' (not a %s)",
+            "<expr> must be 'true' or 'false' or a filter (not a %s)",
             (Int)TNAM_OBJ(opL), 0L );
     }
     
diff --git a/src/intrprtr.c b/src/intrprtr.c
index 68a7d4eae6..882a6ff8e3 100644
--- a/src/intrprtr.c
+++ b/src/intrprtr.c
@@ -1341,13 +1341,25 @@ void            IntrAnd ( void )
     }
 
     /* handle the 'and' of two filters                                    */
-    else if ( IS_OPERATION(opL) ) {
-        if ( IS_OPERATION(opR) ) {
+    else if (IS_PSEUDO_FILTER(opL)) {
+        if (!IS_FILTER(opL)) {
+            // support this for backwards compatibility; see discussion on
+            // https://github.com/gap-system/gap/pull/2732
+            Warning("operation '%g' used in AND-filter is not a filter\n",
+                    (Int)NAME_FUNC(opL), 0);
+        }
+        if (IS_PSEUDO_FILTER(opR)) {
+            if (!IS_FILTER(opR)) {
+                // support this for backwards compatibility; see discussion on
+                // https://github.com/gap-system/gap/pull/2732
+                Warning("operation '%g' used in AND-filter is not a filter",
+                        (Int)NAME_FUNC(opR), 0);
+            }
             PushObj( NewAndFilter( opL, opR ) );
         }
         else {
             ErrorQuit(
-                "<expr> must be 'true' or 'false' (not a %s)",
+                "<expr> must be a filter (not a %s)",
                 (Int)TNAM_OBJ(opL), 0L );
         }
     }
@@ -1355,7 +1367,7 @@ void            IntrAnd ( void )
     /* signal an error                                                     */
     else {
         ErrorQuit(
-            "<expr> must be 'true' or 'false' (not a %s)",
+            "<expr> must be 'true' or 'false' or a filter (not a %s)",
             (Int)TNAM_OBJ(opL), 0L );
     }
 }
diff --git a/src/opers.h b/src/opers.h
index 123e1e3be1..7b67334b6b 100644
--- a/src/opers.h
+++ b/src/opers.h
@@ -247,6 +247,16 @@ static inline Int IS_FILTER(Obj oper)
     return v & OPER_IS_FILTER;
 }
 
+// temporary HACK, until all affected packages are fixed
+static inline Int IS_PSEUDO_FILTER(Obj oper)
+{
+    if (!IS_OPERATION(oper))
+        return 0;
+    Obj flags = FLAGS_FILT(oper);
+    return flags && TNUM_OBJ(flags) == T_FLAGS;
+}
+
+
 /****************************************************************************
 **
 *F  SET_IS_FILTER( <oper> ) . . . . . . . . . . .  mark operation as a filter
diff --git a/tst/testinstall/boolean.tst b/tst/testinstall/boolean.tst
index 8b9514451f..caf921c037 100644
--- a/tst/testinstall/boolean.tst
+++ b/tst/testinstall/boolean.tst
@@ -54,7 +54,17 @@ gap> ViewString(true); ViewString(false); ViewString(fail);
 gap> TNAM_OBJ(fail);
 "boolean or fail"
 
-# test error handling
+# crazy stuff that is accepted by interpreter and executor
+gap> false and 1;
+false
+gap> true or 1;
+true
+gap> function() return false and 1; end();
+false
+gap> function() return true or 1; end();
+true
+
+# test error handling in interpreter
 gap> not 1;
 Error, <expr> must be 'true' or 'false' (not a integer)
 gap> false or 1;
@@ -64,17 +74,64 @@ Error, <expr> must be 'true' or 'false' (not a integer)
 gap> true and 1;
 Error, <expr> must be 'true' or 'false' (not a integer)
 gap> 1 and true;
-Error, <expr> must be 'true' or 'false' (not a integer)
+Error, <expr> must be 'true' or 'false' or a filter (not a integer)
 gap> ReturnTrue and ReturnTrue;
-Error, <expr> must be 'true' or 'false' (not a function)
+Error, <expr> must be 'true' or 'false' or a filter (not a function)
 gap> ReturnTrue and true;
-Error, <expr> must be 'true' or 'false' (not a function)
+Error, <expr> must be 'true' or 'false' or a filter (not a function)
 gap> IsAssociative and ReturnTrue;
-Error, <expr> must be 'true' or 'false' (not a function)
+Error, <expr> must be a filter (not a function)
 gap> IsAssociative and true;
-Error, <expr> must be 'true' or 'false' (not a function)
+Error, <expr> must be a filter (not a function)
+gap> IsAssociative and Center;
+Warning, operation 'Centre' used in AND-filter is not a filter in stream:1
+<Filter "(IsAssociative and Centre)">
+gap> IsAssociative and FirstOp;
+Error, <expr> must be a filter (not a function)
 gap> true and IsAssociative;
 Error, <expr> must be 'true' or 'false' (not a function)
+gap> Center and IsAssociative;
+Warning, operation 'Centre' used in AND-filter is not a filter
+ in stream:1
+<Filter "(Centre and IsAssociative)">
+gap> FirstOp and IsAssociative;
+Error, <expr> must be 'true' or 'false' or a filter (not a function)
+gap> IsAssociative and IsAssociative;
+<Property "IsAssociative">
+
+# test error handling in executor
+gap> function() return not 1; end();
+Error, <expr> must be 'true' or 'false' (not a integer)
+gap> function() return false or 1; end();
+Error, <expr> must be 'true' or 'false' (not a integer)
+gap> function() return 1 or false; end();
+Error, <expr> must be 'true' or 'false' (not a integer)
+gap> function() return true and 1; end();
+Error, <expr> must be 'true' or 'false' (not a integer)
+gap> function() return 1 and true; end();
+Error, <expr> must be 'true' or 'false' or a filter (not a integer)
+gap> function() return ReturnTrue and ReturnTrue; end();
+Error, <expr> must be 'true' or 'false' or a filter (not a function)
+gap> function() return ReturnTrue and true; end();
+Error, <expr> must be 'true' or 'false' or a filter (not a function)
+gap> function() return IsAssociative and ReturnTrue; end();
+Error, <expr> must be a filter (not a function)
+gap> function() return IsAssociative and true; end();
+Error, <expr> must be a filter (not a function)
+gap> function() return IsAssociative and Center; end();
+Warning, operation 'Centre' used in AND-filter is not a filter in stream:1
+<Filter "(IsAssociative and Centre)">
+gap> function() return IsAssociative and FirstOp; end();
+Error, <expr> must be a filter (not a function)
+gap> function() return true and IsAssociative; end();
+Error, <expr> must be 'true' or 'false' (not a function)
+gap> function() return Center and IsAssociative; end();
+Warning, operation 'Centre' used in AND-filter is not a filter in stream:1
+<Filter "(Centre and IsAssociative)">
+gap> function() return FirstOp and IsAssociative; end();
+Error, <expr> must be 'true' or 'false' or a filter (not a function)
+gap> function() return IsAssociative and IsAssociative; end();
+<Property "IsAssociative">
 
 #
 gap> STOP_TEST( "boolean.tst", 1);