diff --git a/src/kaleidoscope/plugin/SpaceCadet.cpp b/src/kaleidoscope/plugin/SpaceCadet.cpp
index 1dc9c75f..0f30c165 100644
--- a/src/kaleidoscope/plugin/SpaceCadet.cpp
+++ b/src/kaleidoscope/plugin/SpaceCadet.cpp
@@ -104,8 +104,9 @@ EventHandlerResult SpaceCadet::onKeyswitchEvent(Key &mapped_key, KeyAddr key_add
 
     //check to see if we found a valid key. Assume not valid.
     bool valid_key = false;
+    bool other_mapped_key_flagged = false;
 
-    //This will only set one key, and, if it isn't in our map, it clears everything for the non-pressed key
+    //Check the current map to see if any other key has been already flagged
     //Exit condition is if we reach the special SPACECADET_MAP_END sentinel
     for (
       uint8_t i = 0 ;
@@ -117,14 +118,37 @@ EventHandlerResult SpaceCadet::onKeyswitchEvent(Key &mapped_key, KeyAddr key_add
       ++i
     ) {
 
-      if (mapped_key == map[i].input) {
-        //The keypress was valid and a match. Mark it as flagged and reset the counter
-        map[i].flagged = true;
-        map[i].start_time = Runtime.millisAtCycleStart();
+      if (map[i].flagged
+          && map[i].input != mapped_key) {
+        other_mapped_key_flagged = true;
+        break;
+      }
+    }
 
-        //yes, we found a valid key
-        valid_key = true;
+    //This will only set one key, and, if it isn't in our map, it clears everything for the non-pressed key
+    //Exit condition is if we reach the special SPACECADET_MAP_END sentinel
+    for (
+      uint8_t i = 0 ;
+      !(
+        map[i].input == Key_NoKey
+        && map[i].output == Key_NoKey
+        && map[i].timeout == 0
+      ) ;
+      ++i
+    ) {
 
+      if (mapped_key == map[i].input) {
+        //Only activate this as part of the mapping if there isn't already a
+        //key waiting for timeout. This allows us to return OK later and for
+        //this loop to inject all the other flagged keys
+        if (!other_mapped_key_flagged) {
+          //The keypress was valid and a match. Mark it as flagged and reset the counter
+          map[i].flagged = true;
+          map[i].start_time = Runtime.millisAtCycleStart();
+
+          //yes, we found a valid key
+          valid_key = true;
+        }
       } else {
         //If the key entry we're looking at was flagged previously, add it to the
         //report before we do anything else (this handles the situation where we