diff --git a/common/core/desktop/include/keyman/keyboardprocessor_debug.h b/common/core/desktop/include/keyman/keyboardprocessor_debug.h
index 2b434b93f5..1b74384b6b 100644
--- a/common/core/desktop/include/keyman/keyboardprocessor_debug.h
+++ b/common/core/desktop/include/keyman/keyboardprocessor_debug.h
@@ -65,10 +65,15 @@ typedef struct {
  */
 
 typedef struct {
-  km_kbp_cp context[DEBUG_MAX_CONTEXT];
+  km_kbp_cp context[DEBUG_MAX_CONTEXT];     // The context matched by the rule (? may not need this?) // TODO: rename to context_matched
   void *group;  // LPGROUP
   void *rule;   // LPKEY
   uint16_t store_offsets[DEBUG_STORE_OFFSETS_SIZE];	// pairs--store, char position, terminated by 0xFFFF // TODO use a better structure here
+
+  /// Track the actions index in the actions that will be returned to
+  /// the debugger; the debugger uses this to determine when to
+  /// execute the actions when single-stepping.
+  uint16_t first_action;
 } km_kbp_state_debug_kmx_info;
 
 /**
diff --git a/common/core/desktop/src/kmx/kmx_debugger.cpp b/common/core/desktop/src/kmx/kmx_debugger.cpp
index b1fa05e388..76ffa1ced0 100644
--- a/common/core/desktop/src/kmx/kmx_debugger.cpp
+++ b/common/core/desktop/src/kmx/kmx_debugger.cpp
@@ -11,7 +11,15 @@
 using namespace km::kbp;
 using namespace kmx;
 
-void KMX_DebugItems::push_item(uint8_t type, uint32_t flags, LPGROUP group, LPKEY key, PKMX_WCHAR context, PKMX_WORD index_stack) {
+void KMX_DebugItems::push_item(
+  uint8_t type,
+  uint32_t flags,
+  LPGROUP group,
+  LPKEY key,
+  PKMX_WCHAR context,
+  PKMX_WORD index_stack,
+  int first_action
+) {
   _items->assert_push_entry();
   km_kbp_state_debug_item item = {type, flags};
   item.kmx_info.rule = key;
@@ -24,6 +32,8 @@ void KMX_DebugItems::push_item(uint8_t type, uint32_t flags, LPGROUP group, LPKE
   }
   item.kmx_info.context[DEBUG_MAX_CONTEXT-1] = 0;
   item.kmx_info.group = group;
+  item.kmx_info.first_action = first_action;
+
   _items->emplace_back(item);
 }
 
diff --git a/common/core/desktop/src/kmx/kmx_debugger.h b/common/core/desktop/src/kmx/kmx_debugger.h
index daddb3463a..e18b394f67 100644
--- a/common/core/desktop/src/kmx/kmx_debugger.h
+++ b/common/core/desktop/src/kmx/kmx_debugger.h
@@ -27,7 +27,8 @@ private:
     LPGROUP group = nullptr,
     LPKEY key = nullptr,
     PKMX_WCHAR context = nullptr,
-    PKMX_WORD index_stack = nullptr
+    PKMX_WORD index_stack = nullptr,
+    int first_action = 0
   );
   void fill_store_offsets(
     km_kbp_state_debug_kmx_info *info,
@@ -39,15 +40,16 @@ public:
   void push_end(uint32_t flags);
   void push_group_enter(LPGROUP group);
   void push_group_exit(LPGROUP group, uint32_t flags);
-  void push_nomatch_enter(LPGROUP group);
+  void push_nomatch_enter(LPGROUP group, int first_action);
   void push_nomatch_exit(LPGROUP group);
-  void push_match_enter(LPGROUP group);
+  void push_match_enter(LPGROUP group, int first_action);
   void push_match_exit(LPGROUP group);
   void push_rule_enter(
     LPGROUP group,
     LPKEY key,
     PKMX_WCHAR context,
-    PKMX_WORD index_stack
+    PKMX_WORD index_stack,
+    int first_action
   );
   void push_rule_exit(
     LPGROUP group,
@@ -90,8 +92,8 @@ KMX_DebugItems::push_group_exit(LPGROUP group, uint32_t flags) {
 }
 
 inline void
-KMX_DebugItems::push_nomatch_enter(LPGROUP group) {
-  push_item(KM_KBP_DEBUG_NOMATCH_ENTER, 0, group);
+KMX_DebugItems::push_nomatch_enter(LPGROUP group, int first_action) {
+  push_item(KM_KBP_DEBUG_NOMATCH_ENTER, 0, group, nullptr, nullptr, nullptr, first_action);
 }
 
 inline void
@@ -100,8 +102,8 @@ KMX_DebugItems::push_nomatch_exit(LPGROUP group) {
 }
 
 inline void
-KMX_DebugItems::push_match_enter(LPGROUP group) {
-  push_item(KM_KBP_DEBUG_MATCH_ENTER, 0, group);
+KMX_DebugItems::push_match_enter(LPGROUP group, int first_action) {
+  push_item(KM_KBP_DEBUG_MATCH_ENTER, 0, group, nullptr, nullptr, nullptr, first_action);
 }
 
 inline void
@@ -114,9 +116,10 @@ KMX_DebugItems::push_rule_enter(
   LPGROUP group,
   LPKEY key,
   PKMX_WCHAR context,
-  PKMX_WORD index_stack
+  PKMX_WORD index_stack,
+  int first_action
 ) {
-  push_item(KM_KBP_DEBUG_RULE_ENTER, 0, group, key, context, index_stack);
+  push_item(KM_KBP_DEBUG_RULE_ENTER, 0, group, key, context, index_stack, first_action);
 }
 
 inline void
diff --git a/common/core/desktop/src/kmx/kmx_processevent.cpp b/common/core/desktop/src/kmx/kmx_processevent.cpp
index b599e481de..656963639b 100644
--- a/common/core/desktop/src/kmx/kmx_processevent.cpp
+++ b/common/core/desktop/src/kmx/kmx_processevent.cpp
@@ -270,7 +270,7 @@ KMX_BOOL KMX_ProcessEvent::ProcessGroup(LPGROUP gp, KMX_BOOL *pOutputKeystroke)
     {
       /* NoMatch rule found, and is a character key */
       if(m_debug_items) {
-        m_debug_items->push_nomatch_enter(gp);
+        m_debug_items->push_nomatch_enter(gp, m_actions.Length());
       }
       PostString(gp->dpNoMatch, m_keyboard.Keyboard, NULL, pOutputKeystroke);
       if(m_debug_items) {
@@ -309,7 +309,7 @@ KMX_BOOL KMX_ProcessEvent::ProcessGroup(LPGROUP gp, KMX_BOOL *pOutputKeystroke)
   m_miniContext[GLOBAL_ContextStackSize-1] = 0;
 
   if(m_debug_items) {
-    m_debug_items->push_rule_enter(gp, kkp, m_miniContext, m_indexStack);
+    m_debug_items->push_rule_enter(gp, kkp, m_miniContext, m_indexStack, m_actions.Length());
   }
 
   /*
@@ -355,7 +355,7 @@ KMX_BOOL KMX_ProcessEvent::ProcessGroup(LPGROUP gp, KMX_BOOL *pOutputKeystroke)
 
   if(shouldProcessNomatch && gp->dpMatch && *gp->dpMatch) {
     if(m_debug_items) {
-      m_debug_items->push_match_enter(gp);
+      m_debug_items->push_match_enter(gp, m_actions.Length());
     }
     PostString(gp->dpMatch, m_keyboard.Keyboard, NULL, pOutputKeystroke);
     if(m_debug_items) {
diff --git a/common/core/desktop/tests/unit/kmnkbd/debug_api.cpp b/common/core/desktop/tests/unit/kmnkbd/debug_api.cpp
index 8f4297b432..f38f38b199 100644
--- a/common/core/desktop/tests/unit/kmnkbd/debug_api.cpp
+++ b/common/core/desktop/tests/unit/kmnkbd/debug_api.cpp
@@ -77,7 +77,7 @@ bool are_store_offsets_equal(const uint16_t (&lhs)[DEBUG_STORE_OFFSETS_SIZE], co
 bool operator==(km_kbp_state_debug_item const & lhs,
                 km_kbp_state_debug_item const & rhs)
 {
-  auto result = (lhs.type == rhs.type && lhs.flags == rhs.flags);
+  auto result = (lhs.type == rhs.type && lhs.flags == rhs.flags && lhs.kmx_info.first_action == rhs.kmx_info.first_action);
   if(result) {
     LPGROUP lgp = static_cast<LPGROUP>(lhs.kmx_info.group), rgp = static_cast<LPGROUP>(rhs.kmx_info.group);
     LPKEY lrule = static_cast<LPKEY>(lhs.kmx_info.rule), rrule = static_cast<LPKEY>(rhs.kmx_info.rule);
@@ -327,9 +327,9 @@ void test_multiple_groups() {
       km_kbp_state_debug_item{KM_KBP_DEBUG_RULE_ENTER, 0, {}, {u"", &gp, &kp1, {0xFFFF}}},
       km_kbp_state_debug_item{KM_KBP_DEBUG_RULE_EXIT, 0, {}, {u"", &gp, &kp1, {0xFFFF}}},
 
-      km_kbp_state_debug_item{KM_KBP_DEBUG_MATCH_ENTER, 0, {}, {u"", &gp}},
+      km_kbp_state_debug_item{KM_KBP_DEBUG_MATCH_ENTER, 0, {}, {u"", &gp, nullptr, {}, 1}},
         km_kbp_state_debug_item{KM_KBP_DEBUG_GROUP_ENTER, 0, {}, {u"", &gpa}},
-          km_kbp_state_debug_item{KM_KBP_DEBUG_RULE_ENTER, 0, {}, {u"a", &gpa, &kpa, {0xFFFF}}},
+          km_kbp_state_debug_item{KM_KBP_DEBUG_RULE_ENTER, 0, {}, {u"a", &gpa, &kpa, {0xFFFF}, 1}},
           km_kbp_state_debug_item{KM_KBP_DEBUG_RULE_EXIT, 0, {}, {u"a", &gpa, &kpa, {0xFFFF}}},
         km_kbp_state_debug_item{KM_KBP_DEBUG_GROUP_EXIT, 0, {}, {u"", &gpa}},
       km_kbp_state_debug_item{KM_KBP_DEBUG_MATCH_EXIT, 0, {}, {u"", &gp}},