diff --git a/packages/tui/src/component/prompt/index.tsx b/packages/tui/src/component/prompt/index.tsx
index 823ca16bef21..da8380a02304 100644
--- a/packages/tui/src/component/prompt/index.tsx
+++ b/packages/tui/src/component/prompt/index.tsx
@@ -461,6 +461,23 @@ export function Prompt(props: PromptProps) {
     syncVimRegisterFromClipboard,
   } = promptVim
 
+  function resetVimHistory() {
+    vimState.resetHistory()
+    if (vimEnabled() && store.mode === "normal" && vimState.isInsert()) vim.beginInsertEdit()
+  }
+
+  createEffect<boolean>((previous) => {
+    const enabled = vimEnabled()
+    if (enabled && previous === false) resetVimHistory()
+    return enabled
+  }, vimEnabled())
+
+  createEffect<"normal" | "shell">((previous) => {
+    const mode = store.mode
+    if (mode !== previous) resetVimHistory()
+    return mode
+  }, store.mode)
+
   createEffect(
     on(
       () => props.sessionID,
@@ -702,7 +719,7 @@ export function Prompt(props: PromptProps) {
           })
           restoreExtmarksFromParts(updatedNonTextParts)
           input.cursorOffset = Bun.stringWidth(normalized)
-          vimState.resetHistory()
+          resetVimHistory()
         },
       },
       {
@@ -734,7 +751,7 @@ export function Prompt(props: PromptProps) {
                   parts: [],
                 })
                 input.gotoBufferEnd()
-                vimState.resetHistory()
+                resetVimHistory()
               }}
             />
           ))
@@ -925,7 +942,7 @@ export function Prompt(props: PromptProps) {
       setStore("prompt", prompt)
       restoreExtmarksFromParts(prompt.parts)
       input.gotoBufferEnd()
-      vimState.resetHistory()
+      resetVimHistory()
     },
     reset() {
       input.clear()
@@ -935,7 +952,7 @@ export function Prompt(props: PromptProps) {
         parts: [],
       })
       setStore("extmarkToPartIndex", new Map())
-      vimState.resetHistory()
+      resetVimHistory()
     },
     submit() {
       void submit()
@@ -945,13 +962,13 @@ export function Prompt(props: PromptProps) {
   onMount(() => {
     const saved = stashed
     stashed = undefined
-    if (store.prompt.input) return
-    if (saved && saved.prompt.input) {
+    if (!store.prompt.input && saved?.prompt.input) {
       input.setText(saved.prompt.input)
       setStore("prompt", saved.prompt)
       restoreExtmarksFromParts(saved.prompt.parts)
       input.cursorOffset = saved.cursor
     }
+    if (vimEnabled() && vimState.isInsert()) vim.beginInsertEdit()
   })
 
   onCleanup(() => {
@@ -1136,6 +1153,7 @@ export function Prompt(props: PromptProps) {
           input.clear()
           setStore("prompt", { input: "", parts: [] })
           setStore("extmarkToPartIndex", new Map())
+          resetVimHistory()
           dialog.clear()
         },
       },
@@ -1151,6 +1169,7 @@ export function Prompt(props: PromptProps) {
             setStore("prompt", { input: entry.input, parts: entry.parts })
             restoreExtmarksFromParts(entry.parts)
             input.gotoBufferEnd()
+            resetVimHistory()
           }
           dialog.clear()
         },
@@ -1168,6 +1187,7 @@ export function Prompt(props: PromptProps) {
                 setStore("prompt", { input: entry.input, parts: entry.parts })
                 restoreExtmarksFromParts(entry.parts)
                 input.gotoBufferEnd()
+                resetVimHistory()
               }}
             />
           ))
@@ -1271,6 +1291,7 @@ export function Prompt(props: PromptProps) {
             setStore("mode", item.mode ?? "normal")
             restoreExtmarksFromParts(item.parts)
             input.cursorOffset = 0
+            resetVimHistory()
           },
         },
       ],
@@ -1307,6 +1328,7 @@ export function Prompt(props: PromptProps) {
             setStore("mode", item.mode ?? "normal")
             restoreExtmarksFromParts(item.parts)
             input.cursorOffset = input.plainText.length
+            resetVimHistory()
           },
         },
       ],
@@ -1532,6 +1554,7 @@ export function Prompt(props: PromptProps) {
       }, 50)
     }
     input.clear()
+    if (vimEnabled() && vimState.isInsert()) vim.beginInsertEdit()
     if (finishMoveProgress) move.finishSubmit()
     return true
   }
@@ -1715,6 +1738,7 @@ export function Prompt(props: PromptProps) {
       parts: [],
     })
     setStore("extmarkToPartIndex", new Map())
+    resetVimHistory()
   }
 
   const dimmed = createMemo(() => leader() || vimState.isCopy())
diff --git a/packages/tui/src/component/prompt/vim.ts b/packages/tui/src/component/prompt/vim.ts
index ab779222b9e8..a3ad483fa8e4 100644
--- a/packages/tui/src/component/prompt/vim.ts
+++ b/packages/tui/src/component/prompt/vim.ts
@@ -50,6 +50,7 @@ export function usePromptVim(opts: {
     popCopyMode?.()
     keymap.setData(OPENCODE_VIM_MODE_KEY, undefined)
     if (vimEnabled()) lastVimMode = vimState.isCopy() ? "normal" : vimState.mode()
+    vimState.cancelEdit()
   })
 
   createEffect(() => {
@@ -93,6 +94,7 @@ export function usePromptVim(opts: {
   function enterCopyMode() {
     const copy = opts.copy()
     if (!vimEnabled() || !copy) return false
+    if (vimState.isInsert()) vim.finishInsertEdit()
     vimState.setMode("copy")
     copy.enter()
     const input = opts.textarea()
diff --git a/packages/tui/src/component/vim/vim-handler.ts b/packages/tui/src/component/vim/vim-handler.ts
index aeccdf5f449c..c72a943287d6 100644
--- a/packages/tui/src/component/vim/vim-handler.ts
+++ b/packages/tui/src/component/vim/vim-handler.ts
@@ -410,6 +410,13 @@ export function createVimHandler(input: {
   const edit = repeat.edit
   const begin = repeat.begin
 
+  function finishInsertEdit() {
+    input.state.setMode("normal")
+    input.state.commitEdit(snapshot())
+    moveLeft(input.textarea())
+    repeat.commit(snapshot())
+  }
+
   function applyOperatorYank(result: VimOperatorResult) {
     if (result.register) setRegister(result.register, true)
     if (result.span && result.span.end > result.span.start) input.flash?.(result.span)
@@ -2271,6 +2278,8 @@ export function createVimHandler(input: {
   }
 
   return {
+    beginInsertEdit: repeat.begin,
+    finishInsertEdit,
     handleKey(event: VimEvent) {
       if (!input.enabled()) return false
 
diff --git a/packages/tui/test/cli/tui/vim-motions.test.ts b/packages/tui/test/cli/tui/vim-motions.test.ts
index 822540bd8d94..c63e7ded967f 100644
--- a/packages/tui/test/cli/tui/vim-motions.test.ts
+++ b/packages/tui/test/cli/tui/vim-motions.test.ts
@@ -8084,6 +8084,50 @@ describe("vim dot repeat", () => {
     expect(ctx.textarea.insertText).toBe(insertText)
   })
 
+  test("tracks implicit insert sessions", () => {
+    const ctx = createHandler("", { mode: "insert" })
+
+    ctx.handler.beginInsertEdit()
+    ctx.textarea.insertText("abc")
+    press(ctx, "escape")
+    press(ctx, "u")
+    expect(ctx.textarea.plainText).toBe("")
+
+    press(ctx, ".")
+    expect(ctx.textarea.plainText).toBe("abc")
+  })
+
+  test("restarts implicit insert tracking after history reset", () => {
+    const ctx = createHandler("draft", { mode: "insert" })
+
+    ctx.handler.beginInsertEdit()
+    ctx.textarea.insertText("!")
+    ctx.state.resetHistory()
+    ctx.textarea.setText("")
+    ctx.handler.beginInsertEdit()
+    ctx.textarea.insertText("abc")
+    press(ctx, "escape")
+    press(ctx, "u")
+    expect(ctx.textarea.plainText).toBe("")
+
+    press(ctx, ".")
+    expect(ctx.textarea.plainText).toBe("abc")
+  })
+
+  test("finishes implicit insert tracking before external mode changes", () => {
+    const ctx = createHandler("", { mode: "insert" })
+
+    ctx.handler.beginInsertEdit()
+    ctx.textarea.insertText("abc")
+    ctx.handler.finishInsertEdit()
+    expect(ctx.textarea.cursorOffset).toBe(2)
+    press(ctx, "u")
+    expect(ctx.textarea.plainText).toBe("")
+
+    press(ctx, ".")
+    expect(ctx.textarea.plainText).toBe("abc")
+  })
+
   test("dot repeats complex insert sessions from the current text", () => {
     const ctx = createHandler("abcd")
     ctx.textarea.cursorOffset = 1