diff --git a/core/continuations/continuations-tests.factor b/core/continuations/continuations-tests.factor
index a6cead0bd9..371c546142 100644
--- a/core/continuations/continuations-tests.factor
+++ b/core/continuations/continuations-tests.factor
@@ -1,6 +1,5 @@
-USING: kernel math namespaces io tools.test sequences vectors
-continuations debugger parser memory arrays words
-kernel.private accessors eval ;
+USING: accessors arrays continuations debugger eval io kernel kernel.private
+math memory namespaces parser sequences system tools.test vectors words ;
 IN: continuations.tests
 
 : (callcc1-test) ( n obj -- n' obj )
@@ -56,6 +55,25 @@ IN: continuations.tests
 ! : callstack-overflow callstack-overflow f ;
 ! [ callstack-overflow ] must-fail
 
+! This tries to verify that enough bytes are cut off from the
+! callstack to run the error handler.
+: pre ( -- ) nano-count 0 = [ ] [ ] if ;
+
+: post ( -- ) ;
+
+: do-overflow ( -- )
+    pre do-overflow post ;
+
+: recurse ( -- ? )
+    [ do-overflow f ] [ ] recover
+    second ERROR-CALLSTACK-OVERFLOW = ;
+
+os windows? [
+    { t } [
+        10 [ recurse ] replicate [ ] all?
+    ] unit-test
+] unless
+
 : don't-compile-me ( -- ) ;
 : foo ( -- ) callstack "c" set don't-compile-me ;
 : bar ( -- a b ) 1 foo 2 ;
diff --git a/vm/contexts.hpp b/vm/contexts.hpp
index c13f3a0444..20d773dea9 100644
--- a/vm/contexts.hpp
+++ b/vm/contexts.hpp
@@ -12,7 +12,11 @@ enum context_object {
   OBJ_IN_CALLBACK_P,
 };
 
-static const cell stack_reserved = 1024;
+/* When the callstack fills up (e.g by to deep recursion), a callstack
+   overflow error is triggered. So before continuing executing on it
+   in general_error(), we chop of this many bytes to have some space
+   to work with. */
+static const cell stack_reserved = 4096;
 
 struct context {
 
diff --git a/vm/cpu-x86.cpp b/vm/cpu-x86.cpp
index 88419b1dab..5ea316169b 100644
--- a/vm/cpu-x86.cpp
+++ b/vm/cpu-x86.cpp
@@ -3,8 +3,9 @@
 namespace factor {
 
 void factor_vm::dispatch_signal_handler(cell* sp, cell* pc, cell handler) {
-  if (!code->seg->in_segment_p(*pc) ||
-      *sp < ctx->callstack_seg->start + stack_reserved) {
+
+  cell callstack_limit = ctx->callstack_seg->start + stack_reserved;
+  if (!code->seg->in_segment_p(*pc) || *sp < callstack_limit) {
     /* Fault came from the VM, foreign code, a callstack overflow, or
        we don't have enough callstack room to try the resumable
        handler. Cut the callstack down to the shallowest Factor stack
@@ -15,8 +16,7 @@ void factor_vm::dispatch_signal_handler(cell* sp, cell* pc, cell handler) {
 
     cell frame_top = ctx->callstack_top;
 
-    while (frame_top < ctx->callstack_bottom &&
-           frame_top < ctx->callstack_seg->start + stack_reserved) {
+    while (frame_top < ctx->callstack_bottom && frame_top < callstack_limit) {
       frame_top = frame_predecessor(frame_top);
     }