diff --git a/packages/opencode/src/session/prompt.ts b/packages/opencode/src/session/prompt.ts
index 4f77920cc987..12512fe099cd 100644
--- a/packages/opencode/src/session/prompt.ts
+++ b/packages/opencode/src/session/prompt.ts
@@ -320,6 +320,12 @@ export namespace SessionPrompt {
         !["tool-calls", "unknown"].includes(lastAssistant.finish) &&
         lastUser.id < lastAssistant.id
       ) {
+        const hook = await Plugin.trigger("session.stopping", { sessionID }, { stop: true, message: undefined as string | undefined })
+        if (!hook.stop && hook.message) {
+          log.info("session.stopping hook prevented stop", { sessionID })
+          await createUserMessage({ sessionID, parts: [{ type: "text", text: hook.message }] })
+          continue
+        }
         log.info("exiting loop", { sessionID })
         break
       }
diff --git a/packages/opencode/test/plugin/session-stopping.test.ts b/packages/opencode/test/plugin/session-stopping.test.ts
new file mode 100644
index 000000000000..83704bd126b6
--- /dev/null
+++ b/packages/opencode/test/plugin/session-stopping.test.ts
@@ -0,0 +1,120 @@
+import { describe, expect, test } from "bun:test"
+import path from "path"
+import fs from "fs/promises"
+import { tmpdir } from "../fixture/fixture"
+import { Instance } from "../../src/project/instance"
+import { Plugin } from "../../src/plugin"
+import { Session } from "../../src/session"
+import { SessionPrompt } from "../../src/session/prompt"
+
+describe("session.stopping hook", () => {
+  test("plugin with session.stopping hook loads and triggers correctly", async () => {
+    await using tmp = await tmpdir({
+      init: async (dir) => {
+        const pluginDir = path.join(dir, ".opencode", "plugin")
+        await fs.mkdir(pluginDir, { recursive: true })
+        await Bun.write(
+          path.join(pluginDir, "stop-hook.ts"),
+          [
+            "export default async () => ({",
+            '  "session.stopping": async (input, output) => {',
+            "    output.stop = false",
+            '    output.message = "workflow gate"',
+            "  },",
+            "})",
+          ].join("\n"),
+        )
+      },
+    })
+
+    await Instance.provide({
+      directory: tmp.path,
+      fn: async () => {
+        await Plugin.init()
+        const out = await Plugin.trigger("session.stopping", { sessionID: "test-session" }, { stop: true, message: undefined as string | undefined })
+        expect(out.stop).toBe(false)
+        expect(out.message).toBe("workflow gate")
+      },
+    })
+  }, 30000)
+
+  test("no plugin installed — stop stays true", async () => {
+    await using tmp = await tmpdir()
+    await Instance.provide({
+      directory: tmp.path,
+      fn: async () => {
+        await Plugin.init()
+        const out = await Plugin.trigger("session.stopping", { sessionID: "test-session" }, { stop: true, message: undefined as string | undefined })
+        expect(out.stop).toBe(true)
+        expect(out.message).toBeUndefined()
+      },
+    })
+  }, 30000)
+
+  test("stop=false without message does not satisfy re-entry condition", async () => {
+    await using tmp = await tmpdir({
+      init: async (dir) => {
+        const pluginDir = path.join(dir, ".opencode", "plugin")
+        await fs.mkdir(pluginDir, { recursive: true })
+        await Bun.write(
+          path.join(pluginDir, "no-msg.ts"),
+          ["export default async () => ({", '  "session.stopping": async (_input, output) => {', "    output.stop = false", "  },", "})"].join("\n"),
+        )
+      },
+    })
+    await Instance.provide({
+      directory: tmp.path,
+      fn: async () => {
+        await Plugin.init()
+        const out = await Plugin.trigger("session.stopping", { sessionID: "test-session" }, { stop: true, message: undefined as string | undefined })
+        expect(out.stop).toBe(false)
+        expect(out.message).toBeUndefined()
+      },
+    })
+  }, 30000)
+
+  test("hook message is persisted as a user message in the session", async () => {
+    await using tmp = await tmpdir({
+      git: true,
+      init: async (dir) => {
+        const pluginDir = path.join(dir, ".opencode", "plugin")
+        await fs.mkdir(pluginDir, { recursive: true })
+        await Bun.write(
+          path.join(pluginDir, "gate.ts"),
+          [
+            "export default async () => ({",
+            '  "session.stopping": async (_input, output) => {',
+            "    output.stop = false",
+            '    output.message = "resume from gate"',
+            "  },",
+            "})",
+          ].join("\n"),
+        )
+      },
+    })
+
+    await Instance.provide({
+      directory: tmp.path,
+      fn: async () => {
+        await Plugin.init()
+        const session = await Session.create({})
+
+        const out = await Plugin.trigger("session.stopping", { sessionID: session.id }, { stop: true, message: undefined as string | undefined })
+        expect(out.stop).toBe(false)
+        expect(out.message).toBe("resume from gate")
+
+        const msg = await SessionPrompt.prompt({
+          sessionID: session.id,
+          noReply: true,
+          parts: [{ type: "text", text: out.message! }],
+        })
+
+        expect(msg.info.role).toBe("user")
+        const text = msg.parts.find((p) => p.type === "text" && !p.synthetic)
+        expect(text?.type === "text" && text.text).toBe("resume from gate")
+
+        await Session.remove(session.id)
+      },
+    })
+  }, 30000)
+})
diff --git a/packages/plugin/src/index.ts b/packages/plugin/src/index.ts
index 76370d1d5a7f..5fb0b1c37b06 100644
--- a/packages/plugin/src/index.ts
+++ b/packages/plugin/src/index.ts
@@ -231,4 +231,12 @@ export interface Hooks {
    * Modify tool definitions (description and parameters) sent to LLM
    */
   "tool.definition"?: (input: { toolID: string }, output: { description: string; parameters: any }) => Promise<void>
+  /**
+   * Called before the agent loop exits. Set `output.stop = false` and
+   * provide `output.message` to inject a user message and continue the loop.
+   */
+  "session.stopping"?: (
+    input: { sessionID: string },
+    output: { stop: boolean; message?: string },
+  ) => Promise<void>
 }