diff --git a/packages/debugger/lib/controller/sagas/index.js b/packages/debugger/lib/controller/sagas/index.js
index 522c3f6600e..2e7e80bb12c 100644
--- a/packages/debugger/lib/controller/sagas/index.js
+++ b/packages/debugger/lib/controller/sagas/index.js
@@ -78,9 +78,12 @@ function* advance(action) {
  */
 function* stepNext() {
   const starting = yield select(controller.current.location);
+  const isStartingGenerated = yield select(
+    controller.current.isAnyFrameGenerated
+  );
   const allowInternal = yield select(controller.stepIntoInternalSources);
 
-  let upcoming, finished;
+  let upcoming, finished, isUpcomingGenerated;
 
   do {
     // advance at least once step
@@ -88,6 +91,7 @@ function* stepNext() {
 
     // and check the next source range
     upcoming = yield select(controller.current.location);
+    isUpcomingGenerated = yield select(controller.current.isAnyFrameGenerated);
 
     finished = yield select(controller.current.trace.finished);
 
@@ -98,8 +102,8 @@ function* stepNext() {
       //don't stop on an internal source unless allowInternal is on or
       //we started in an internal source
       (!allowInternal &&
-        upcoming.source.internal &&
-        !starting.source.internal) ||
+        (upcoming.source.internal || isUpcomingGenerated) &&
+        !(starting.source.internal || isStartingGenerated)) ||
       upcoming.sourceRange.length === 0 ||
       upcoming.source.id === undefined ||
       (upcoming.node && isDeliberatelySkippedNodeType(upcoming.node)) ||
diff --git a/packages/debugger/lib/controller/selectors/index.js b/packages/debugger/lib/controller/selectors/index.js
index a8f8552311d..7a591673fc6 100644
--- a/packages/debugger/lib/controller/selectors/index.js
+++ b/packages/debugger/lib/controller/selectors/index.js
@@ -7,6 +7,7 @@ import * as Codec from "@truffle/codec";
 
 import evm from "lib/evm/selectors";
 import sourcemapping from "lib/sourcemapping/selectors";
+import stacktrace from "lib/stacktrace/selectors";
 import data from "lib/data/selectors";
 import trace from "lib/trace/selectors";
 
@@ -137,6 +138,24 @@ const controller = createSelectorTree({
       )
     },
 
+    /**
+     * controller.current.callstack
+     */
+    callstack: createLeaf([stacktrace.current.callstack.preupdated], identity),
+
+    /**
+     * controller.current.isAnyFrameGenerated
+     *
+     * This selector checks whether there are any generated sources
+     * stackframes on the callstack.  We should regard ourselves
+     * as still inside a generated source until there are none.
+     * (We only consider generated sources here, not other sorts of internal
+     * sources, to prevent potential problems.)
+     */
+    isAnyFrameGenerated: createLeaf(["./callstack"], callstack =>
+      callstack.some(frame => frame.sourceIsGenerated)
+    ),
+
     /**
      * controller.current.trace
      */
diff --git a/packages/debugger/lib/stacktrace/actions/index.js b/packages/debugger/lib/stacktrace/actions/index.js
index 4e88bff61fb..d9dd0c47f3c 100644
--- a/packages/debugger/lib/stacktrace/actions/index.js
+++ b/packages/debugger/lib/stacktrace/actions/index.js
@@ -1,11 +1,18 @@
 export const JUMP_IN = "STACKTRACE_JUMP_IN";
-export function jumpIn(location, functionNode, contractNode, sourceIsInternal) {
+export function jumpIn(
+  location,
+  functionNode,
+  contractNode,
+  sourceIsInternal,
+  sourceIsGenerated
+) {
   return {
     type: JUMP_IN,
     location,
     functionNode,
     contractNode,
-    sourceIsInternal
+    sourceIsInternal,
+    sourceIsGenerated
   };
 }
 
diff --git a/packages/debugger/lib/stacktrace/reducers.js b/packages/debugger/lib/stacktrace/reducers.js
index 540f1b50c0c..8db98c85fd0 100644
--- a/packages/debugger/lib/stacktrace/reducers.js
+++ b/packages/debugger/lib/stacktrace/reducers.js
@@ -10,7 +10,13 @@ function callstack(state = [], action) {
   let newFrame;
   switch (action.type) {
     case actions.JUMP_IN:
-      const { location, functionNode, contractNode, sourceIsInternal } = action;
+      const {
+        location,
+        functionNode,
+        contractNode,
+        sourceIsInternal,
+        sourceIsGenerated
+      } = action;
       newFrame = {
         type: "internal",
         calledFromLocation: location,
@@ -27,7 +33,8 @@ function callstack(state = [], action) {
             ? contractNode.name
             : undefined,
         combineWithNextInternal: false,
-        sourceIsInternal
+        sourceIsInternal,
+        sourceIsGenerated
         //note we don't currently account for getters because currently
         //we can't; fallback, receive, constructors, & modifiers also remain
         //unaccounted for at present
diff --git a/packages/debugger/lib/stacktrace/sagas/index.js b/packages/debugger/lib/stacktrace/sagas/index.js
index 6a37752f5c9..6a866b650a0 100644
--- a/packages/debugger/lib/stacktrace/sagas/index.js
+++ b/packages/debugger/lib/stacktrace/sagas/index.js
@@ -63,12 +63,16 @@ function* stacktraceSaga() {
     const nextLocation = yield select(stacktrace.next.location);
     const nextParent = yield select(stacktrace.next.contractNode);
     const nextSourceIsInternal = yield select(stacktrace.next.sourceIsInternal);
+    const nextSourceIsGenerated = yield select(
+      stacktrace.next.sourceIsGenerated
+    );
     yield put(
       actions.jumpIn(
         currentLocation,
         nextLocation.node,
         nextParent,
-        nextSourceIsInternal
+        nextSourceIsInternal,
+        nextSourceIsGenerated
       )
     );
     positionUpdated = true;
diff --git a/packages/debugger/lib/stacktrace/selectors/index.js b/packages/debugger/lib/stacktrace/selectors/index.js
index b7746af6faf..bf11ae9a8bb 100644
--- a/packages/debugger/lib/stacktrace/selectors/index.js
+++ b/packages/debugger/lib/stacktrace/selectors/index.js
@@ -111,6 +111,15 @@ function createMultistepSelectors(stepSelector) {
       source => source.id === undefined || source.internal
     ),
 
+    /**
+     * .sourceIsGenerated
+     * only specifically generated sources, not unmapped code or anything!
+     */
+    sourceIsGenerated: createLeaf(
+      ["./location/source"],
+      source => source.internal
+    ),
+
     /**
      * .strippedLocation
      */
@@ -156,9 +165,31 @@ let stacktrace = createSelectorTree({
    */
   current: {
     /**
-     * stacktrace.current.callstack
+     * stacktrace.current.callstack (namespace)
      */
-    callstack: createLeaf(["/state"], state => state.proc.callstack),
+    callstack: {
+      /**
+       * stacktrace.current.callstack (selector)
+       */
+      _: createLeaf(["/state"], state => state.proc.callstack),
+
+      /**
+       * stacktrace.current.callstack.preupdated
+       * This selector reflects the callstack as it actually is at the current
+       * moment, rather than carrying around additional error information on top
+       * in case it turns out to be relevant -- it's been "preupdated" assuming
+       * we don't want the error info on top, which in certain cases, we don't.
+       */
+      preupdated: createLeaf(
+        ["./_", "/current/returnCounter"],
+        (callstack, returnCounter) =>
+          popNWhere(
+            callstack,
+            returnCounter,
+            frame => frame.type === "external"
+          )
+      )
+    },
 
     /**
      * stacktrace.current.returnCounter
@@ -398,18 +429,14 @@ let stacktrace = createSelectorTree({
      */
     report: createLeaf(
       [
-        "./callstack",
+        "./callstack/preupdated",
         "./returnCounter",
         "./lastPosition",
         "/current/strippedLocation"
       ],
       (callstack, returnCounter, lastPosition, currentLocation) =>
         generateReport(
-          popNWhere(
-            callstack,
-            returnCounter,
-            frame => frame.type === "external"
-          ),
+          callstack,
           currentLocation || lastPosition,
           null,
           undefined