diff --git a/src/state/searchState.ts b/src/state/searchState.ts
index 8646d3e39d4..8d1ebb823ae 100644
--- a/src/state/searchState.ts
+++ b/src/state/searchState.ts
@@ -325,7 +325,7 @@ export class SearchState {
         .slice(0)
         .reverse()
         .entries()) {
-        if (matchRange.start.compareTo(startPosition) < 0) {
+        if (matchRange.end.compareTo(startPosition) <= 0) {
           return {
             start: Position.FromVSCodePosition(matchRange.start),
             end: Position.FromVSCodePosition(matchRange.end),
diff --git a/test/mode/normalModeTests/motions.test.ts b/test/mode/normalModeTests/motions.test.ts
index 6a0605b49fe..898a1c7ef51 100644
--- a/test/mode/normalModeTests/motions.test.ts
+++ b/test/mode/normalModeTests/motions.test.ts
@@ -312,6 +312,13 @@ suite('Motions in Normal Mode', () => {
     end: ['one two |two two'],
   });
 
+  newTest({
+    title: 'Can run a forward and find previous search from end of word',
+    start: ['|one two one two'],
+    keysPressed: '/two/e\nN',
+    end: ['one two one tw|o'],
+  });
+
   // These "remembering history between editor" tests have started
   // breaking. Since I don't remember these tests ever breaking for real, and
   // because they're the cause of a lot of flaky tests, I'm disabling these for