diff --git a/src/core_editor/editor.rs b/src/core_editor/editor.rs
index 0d7673ba..feb64542 100644
--- a/src/core_editor/editor.rs
+++ b/src/core_editor/editor.rs
@@ -306,7 +306,16 @@ impl Editor {
     }
 
     pub(crate) fn is_cursor_at_buffer_end(&self) -> bool {
-        self.line_buffer.insertion_point() == self.get_buffer().len()
+        let pos = self.line_buffer.insertion_point();
+        let len = self.get_buffer().len();
+        if pos == len {
+            return true;
+        }
+        // In Vi normal mode the cursor sits *on* the last character rather
+        // than after it.  Treat that position as "at buffer end" so that
+        // prefix history search still triggers after pressing Escape.
+        matches!(self.edit_mode, PromptEditMode::Vi(PromptViMode::Normal))
+            && self.line_buffer.grapheme_right_index() == len
     }
 
     pub(crate) fn reset_undo_stack(&mut self) {
@@ -2168,4 +2177,39 @@ mod test {
         assert_eq!(bracket_result, expected_bracket);
         assert_eq!(quote_result, expected_quote);
     }
+
+    #[test]
+    fn test_is_cursor_at_buffer_end_vi_normal_mode() {
+        // In Vi normal mode, the cursor on the last character should count
+        // as "at buffer end" for prefix history search purposes.
+        let mut editor = editor_with("ls");
+        editor.set_edit_mode(PromptEditMode::Vi(PromptViMode::Normal));
+
+        // Cursor on last char 's' (position 1)
+        editor.line_buffer.set_insertion_point(1);
+        assert!(editor.is_cursor_at_buffer_end());
+
+        // Cursor on first char 'l' (position 0) — not at end
+        editor.line_buffer.set_insertion_point(0);
+        assert!(!editor.is_cursor_at_buffer_end());
+
+        // Cursor after last char (position 2) — still at end
+        editor.line_buffer.set_insertion_point(2);
+        assert!(editor.is_cursor_at_buffer_end());
+    }
+
+    #[test]
+    fn test_is_cursor_at_buffer_end_insert_mode() {
+        // In insert mode, only cursor after the last character counts.
+        let mut editor = editor_with("ls");
+        editor.set_edit_mode(PromptEditMode::Vi(PromptViMode::Insert));
+
+        // Cursor on last char 's' (position 1) — NOT at end in insert mode
+        editor.line_buffer.set_insertion_point(1);
+        assert!(!editor.is_cursor_at_buffer_end());
+
+        // Cursor after last char (position 2) — at end
+        editor.line_buffer.set_insertion_point(2);
+        assert!(editor.is_cursor_at_buffer_end());
+    }
 }
diff --git a/src/edit_mode/vi/mod.rs b/src/edit_mode/vi/mod.rs
index 721e45d9..216a1fc3 100644
--- a/src/edit_mode/vi/mod.rs
+++ b/src/edit_mode/vi/mod.rs
@@ -156,8 +156,20 @@ impl EditMode for Vi {
                 }
                 (_, KeyModifiers::NONE, KeyCode::Esc) => {
                     self.cache.clear();
+                    let was_insert = self.mode == ViMode::Insert;
                     self.mode = ViMode::Normal;
-                    ReedlineEvent::Multiple(vec![ReedlineEvent::Esc, ReedlineEvent::Repaint])
+                    // In Vi, exiting insert mode moves the cursor one position
+                    // left because insert mode places the cursor between
+                    // characters while normal mode places it on a character.
+                    if was_insert {
+                        ReedlineEvent::Multiple(vec![
+                            ReedlineEvent::Edit(vec![EditCommand::MoveLeft { select: false }]),
+                            ReedlineEvent::Esc,
+                            ReedlineEvent::Repaint,
+                        ])
+                    } else {
+                        ReedlineEvent::Multiple(vec![ReedlineEvent::Esc, ReedlineEvent::Repaint])
+                    }
                 }
                 (ViMode::Normal | ViMode::Visual, _, _) => self
                     .normal_keybindings
@@ -231,13 +243,41 @@ mod test {
     use pretty_assertions::assert_eq;
 
     #[test]
-    fn esc_leads_to_normal_mode_test() {
+    fn esc_from_insert_mode_moves_cursor_left() {
         let mut vi = Vi::default();
+        assert!(matches!(vi.mode, ViMode::Insert));
+
+        let esc =
+            ReedlineRawEvent::try_from(Event::Key(KeyEvent::new(KeyCode::Esc, KeyModifiers::NONE)))
+                .unwrap();
+        let result = vi.parse_event(esc);
+
+        // Exiting insert mode should move the cursor left (Vi standard
+        // behavior: insert mode cursor is between characters, normal mode
+        // cursor is on a character).
+        assert_eq!(
+            result,
+            ReedlineEvent::Multiple(vec![
+                ReedlineEvent::Edit(vec![EditCommand::MoveLeft { select: false }]),
+                ReedlineEvent::Esc,
+                ReedlineEvent::Repaint,
+            ])
+        );
+        assert!(matches!(vi.mode, ViMode::Normal));
+    }
+
+    #[test]
+    fn esc_from_normal_mode_does_not_move_cursor() {
+        let mut vi = Vi {
+            mode: ViMode::Normal,
+            ..Default::default()
+        };
         let esc =
             ReedlineRawEvent::try_from(Event::Key(KeyEvent::new(KeyCode::Esc, KeyModifiers::NONE)))
                 .unwrap();
         let result = vi.parse_event(esc);
 
+        // Esc from normal mode should NOT move the cursor left.
         assert_eq!(
             result,
             ReedlineEvent::Multiple(vec![ReedlineEvent::Esc, ReedlineEvent::Repaint])