diff --git a/libs/iovm/source/IoObject.c b/libs/iovm/source/IoObject.c
index 4aa9139e8..d85e0699a 100644
--- a/libs/iovm/source/IoObject.c
+++ b/libs/iovm/source/IoObject.c
@@ -124,6 +124,7 @@ IoObject *IoObject_protoFinish(void *state)
 	{">", IoObject_isGreaterThan_},
 	{">=", IoObject_isGreaterThanOrEqualTo_},
 	{"<=", IoObject_isLessThanOrEqualTo_},
+	{"asBoolean", IoObject_asBoolean},
 
 	// comparison
 
@@ -1765,6 +1766,14 @@ IO_METHOD(IoObject, isLessThanOrEqualTo_)
 	return IOBOOL(self, IoObject_compare(self, v) <= 0);
 }
 
+IO_METHOD(IoObject, asBoolean)
+{
+	if (self == IOSTATE->ioFalse || self == IOSTATE->ioNil)
+		return self;
+	else
+		return IOSTATE->ioTrue;
+}
+
 IO_METHOD(IoObject, isGreaterThan_)
 {
 	/*doc Object >(expression)
@@ -1819,8 +1828,8 @@ IO_METHOD(IoObject, do)
 IO_METHOD(IoObject, lexicalDo)
 {
 	/*doc Object lexicalDo(expression)
-	Evaluates the message in the context of the receiver. 
-	The lexical context is added as a proto of the receiver while the argument is evaluated. 
+	Evaluates the message in the context of the receiver.
+	The lexical context is added as a proto of the receiver while the argument is evaluated.
 	Returns self.
 	*/
 
diff --git a/libs/iovm/source/IoObject.h b/libs/iovm/source/IoObject.h
index 0ce89ab20..f9b942ee8 100644
--- a/libs/iovm/source/IoObject.h
+++ b/libs/iovm/source/IoObject.h
@@ -177,6 +177,7 @@ IOVM_API IO_METHOD(IoObject, isLessThan_);
 IOVM_API IO_METHOD(IoObject, isLessThanOrEqualTo_);
 IOVM_API IO_METHOD(IoObject, isGreaterThan_);
 IOVM_API IO_METHOD(IoObject, isGreaterThanOrEqualTo_);
+IOVM_API IO_METHOD(IoObject, asBoolean);
 
 // meta
 
diff --git a/libs/iovm/source/IoObject_flow.c b/libs/iovm/source/IoObject_flow.c
index c1823df22..e15182f4f 100644
--- a/libs/iovm/source/IoObject_flow.c
+++ b/libs/iovm/source/IoObject_flow.c
@@ -25,7 +25,8 @@ IO_METHOD(IoObject, while)
 		{
 			IoState_clearTopPool(state);
 			IoState_stackRetain_(state, result);
-			c = ISTRUE(IoMessage_locals_valueArgAt_(m, locals, 0));
+			IoObject *v = IoMessage_locals_valueArgAt_(m, locals, 0);
+			c = ISTRUE(IoMessage_locals_performOn_(IOSTATE->asBooleanMessage, v, v));
 
 			if (!c)
 			{
@@ -80,7 +81,7 @@ IO_METHOD(IoObject, loop)
 IO_METHOD(IoObject, for)
 {
 	/*doc Object for(<counter>, <start>, <end>, <do message>)
-	A for-loop control structure. See the io Programming Guide for a full description. 
+	A for-loop control structure. See the io Programming Guide for a full description.
 	*/
 
 	IoMessage_assertArgCount_receiver_(m, 4, self);
@@ -165,7 +166,7 @@ IO_METHOD(IoObject, return)
 IO_METHOD(IoObject, returnIfNonNil)
 {
 	/*doc Object returnIfNonNil
-	Returns the receiver from the current execution block if it is non nil. 
+	Returns the receiver from the current execution block if it is non nil.
 	Otherwise returns the receiver locally.
 	*/
 
@@ -180,7 +181,7 @@ IO_METHOD(IoObject, returnIfNonNil)
 IO_METHOD(IoObject, break)
 {
 	/*doc Object break(optionalReturnValue)
-	Break the current loop, if any. 
+	Break the current loop, if any.
 	*/
 
 	IoObject *v = IONIL(self);
@@ -198,7 +199,7 @@ IO_METHOD(IoObject, continue)
 {
 	/*doc Object continue
 	Skip the rest of the current loop iteration and start on
-	the next, if any. 
+	the next, if any.
 	*/
 
 	IoState_continue(IOSTATE);
@@ -229,8 +230,8 @@ IO_METHOD(IoObject, if)
 	Returns the result of the evaluated message or Nil if none was evaluated.
 	*/
 
-	const IoObject *const r = IoMessage_locals_valueArgAt_(m, locals, 0);
-	const int condition = ISTRUE((IoObject *)r);
+	IoObject *r = IoMessage_locals_valueArgAt_(m, locals, 0);
+	const int condition = ISTRUE(IoMessage_locals_performOn_(IOSTATE->asBooleanMessage, r, r));
 	const int index = condition ? 1 : 2;
 
 	if (index < IoMessage_argCount(m))
diff --git a/libs/iovm/source/IoState.c b/libs/iovm/source/IoState.c
index 5bf42424b..32b731cde 100644
--- a/libs/iovm/source/IoState.c
+++ b/libs/iovm/source/IoState.c
@@ -215,7 +215,7 @@ void IoState_new_atAddress(void *address)
 
 		//IoState_popCollectorPause(self);
 		IoState_clearRetainStack(self);
-	
+
 		//Collector_check(self->collector);
 		Collector_collect(self->collector);
 		//io_show_mem("after IoState_clearRetainStack and Collector_collect");
@@ -324,7 +324,7 @@ void IoState_setupCachedMessages(IoState *self)
 {
 	self->asStringMessage = IoMessage_newWithName_(self, SIOSYMBOL("asString"));
 	IoState_retain_(self, self->asStringMessage);
-	
+
 	self->collectedLinkMessage = IoMessage_newWithName_(self, SIOSYMBOL("collectedLink"));
 	IoState_retain_(self, self->collectedLinkMessage);
 
@@ -333,10 +333,10 @@ void IoState_setupCachedMessages(IoState *self)
 
 	//self->doStringMessage = IoMessage_newWithName_(self, SIOSYMBOL("doString"));
 	//IoState_retain_(self, self->doStringMessage);
-	
+
 	self->initMessage = IoMessage_newWithName_(self, SIOSYMBOL("init"));
 	IoState_retain_(self, self->initMessage);
-	
+
 	self->mainMessage = IoMessage_newWithName_(self, SIOSYMBOL("main"));
 	IoState_retain_(self, self->mainMessage);
 
@@ -351,7 +351,7 @@ void IoState_setupCachedMessages(IoState *self)
 
 	self->objectForReferenceIdMessage = IoMessage_newWithName_(self, SIOSYMBOL("objectForReferenceId"));
 	IoState_retain_(self, self->objectForReferenceIdMessage);
-			
+
 	self->runMessage = IoMessage_newWithName_(self, SIOSYMBOL("run"));
 	IoState_retain_(self, self->runMessage);
 
@@ -360,9 +360,12 @@ void IoState_setupCachedMessages(IoState *self)
 
 	self->yieldMessage = IoMessage_newWithName_(self, SIOSYMBOL("yield"));
 	IoState_retain_(self, self->yieldMessage);
-	
+
 	self->didFinishMessage = IoMessage_newWithName_(self, SIOSYMBOL("didFinish"));
 	IoState_retain_(self, self->didFinishMessage);
+
+	self->asBooleanMessage = IoMessage_newWithName_(self, SIOSYMBOL("asBoolean"));
+	IoState_retain_(self, self->asBooleanMessage);
 }
 
 IO_METHOD(IoObject, initBindings)
@@ -395,7 +398,7 @@ void IoState_registerProtoWithNamed_(IoState *self, IoObject *proto, const char
 		printf("Error registering proto: %s\n", IoObject_name(proto));
 		IoState_fatalError_(self, "IoState_registerProtoWithFunc_() Error: attempt to add the same proto twice");
 	}
-	
+
 	IoState_retain_(self, proto);
 	PointerHash_at_put_(self->primitives, (void *)func, proto);
 	//printf("registered %s\n", IoObject_name(proto));
@@ -566,7 +569,7 @@ void IoState_runCLI(IoState *self)
 {
 	IoObject *result = IoState_on_doCString_withLabel_(self, self->lobby, "CLI run", "IoState_runCLI()");
 	IoObject *e = IoCoroutine_rawException(self->currentCoroutine);
-	
+
 	if (e != self->ioNil)
 	{
 		self->exitResult = -1;
diff --git a/libs/iovm/source/IoState.h b/libs/iovm/source/IoState.h
index 088ebcb73..0118a0e6b 100644
--- a/libs/iovm/source/IoState.h
+++ b/libs/iovm/source/IoState.h
@@ -14,7 +14,7 @@
 #include "CHash.h"
 #include "MainArgs.h"
 #include "IoObject_struct.h"
-#include "RandomGen.h" 
+#include "RandomGen.h"
 #define COLLECTOROBJECTTYPE IoObjectData
 
 #include "Collector.h"
@@ -66,7 +66,7 @@ struct IoState
 	IoSymbol *stackSizeSymbol;
 	IoSymbol *typeSymbol;
 	IoSymbol *updateSlotSymbol;
-	
+
 	IoSymbol *runTargetSymbol;
 	IoSymbol *runMessageSymbol;
 	IoSymbol *runLocalsSymbol;
@@ -93,6 +93,7 @@ struct IoState
 	IoMessage *willFreeMessage;
 	IoMessage *yieldMessage;
 	IoMessage *didFinishMessage;
+	IoMessage *asBooleanMessage;
 
 	List *cachedNumbers;
 
@@ -156,10 +157,10 @@ struct IoState
 
 	int shouldExit;
 	int exitResult;
-	
+
 	int receivedSignal;
 	int showAllMessages;
-	
+
 	//CHash *profiler;
 };