diff --git a/packages/agent/src/server/agent-server.ts b/packages/agent/src/server/agent-server.ts
index 12ea84c47..90e35a8ec 100644
--- a/packages/agent/src/server/agent-server.ts
+++ b/packages/agent/src/server/agent-server.ts
@@ -1153,6 +1153,7 @@ export class AgentServer {
 
       if (result.stopReason === "end_turn") {
         await this.relayAgentResponse(payload);
+        await this.maybeCompleteAutomationRun(payload, taskRun);
       }
     } catch (error) {
       this.logger.error("Failed to send initial task message", error);
@@ -1276,6 +1277,7 @@ export class AgentServer {
 
       if (result.stopReason === "end_turn") {
         await this.relayAgentResponse(payload);
+        await this.maybeCompleteAutomationRun(payload, taskRun);
       }
     } catch (error) {
       this.logger.error("Failed to send resume message", error);
@@ -1744,6 +1746,37 @@ ${attributionInstructions}
     }
   }
 
+  private shouldAutoCompleteAutomationRun(taskRun: TaskRun | null): boolean {
+    const state = taskRun?.state;
+    return Boolean(
+      state &&
+        typeof state === "object" &&
+        typeof state.automation_id === "string" &&
+        state.automation_id.trim().length > 0,
+    );
+  }
+
+  private async maybeCompleteAutomationRun(
+    payload: JwtPayload,
+    taskRun: TaskRun | null,
+  ): Promise<void> {
+    if (!this.shouldAutoCompleteAutomationRun(taskRun)) {
+      return;
+    }
+
+    try {
+      await this.posthogAPI.updateTaskRun(payload.task_id, payload.run_id, {
+        status: "completed",
+      });
+      this.logger.debug("Automation run marked completed after end_turn", {
+        taskId: payload.task_id,
+        runId: payload.run_id,
+      });
+    } catch (error) {
+      this.logger.error("Failed to mark automation run completed", error);
+    }
+  }
+
   private async signalTaskComplete(
     payload: JwtPayload,
     stopReason: string,
diff --git a/packages/agent/src/server/question-relay.test.ts b/packages/agent/src/server/question-relay.test.ts
index daf597ec1..d37d536e4 100644
--- a/packages/agent/src/server/question-relay.test.ts
+++ b/packages/agent/src/server/question-relay.test.ts
@@ -2,6 +2,7 @@ import { type SetupServerApi, setupServer } from "msw/node";
 import { afterEach, beforeEach, describe, expect, it, vi } from "vitest";
 import { classifyAgentError } from "../adapters/claude/conversion/sdk-to-acp";
 import type { PostHogAPIClient } from "../posthog-api";
+import type { ResumeState } from "../resume";
 import { createTestRepo, type TestRepo } from "../test/fixtures/api";
 import { createPostHogHandlers } from "../test/mocks/msw-handlers";
 import type { Task, TaskRun } from "../types";
@@ -22,9 +23,11 @@ interface TestableAgentServer {
     }>;
   };
   questionRelayedToSlack: boolean;
+  resumeState: ResumeState | null;
   session: unknown;
   relayAgentResponse: (payload: Record<string, unknown>) => Promise<void>;
   sendInitialTaskMessage: (payload: Record<string, unknown>) => Promise<void>;
+  syncCloudBranchMetadata: (payload: Record<string, unknown>) => Promise<void>;
 }
 
 const TEST_PAYLOAD = {
@@ -457,6 +460,7 @@ describe("Question relay", () => {
         acpSessionId: "acp-session",
         clientConnection: { prompt: promptSpy },
         logWriter: {
+          appendRawLine: vi.fn(),
           flushAll: vi.fn().mockResolvedValue(undefined),
           getFullAgentResponse: vi.fn().mockReturnValue(null),
           resetTurnMessages: vi.fn(),
@@ -501,6 +505,7 @@ describe("Question relay", () => {
         acpSessionId: "acp-session",
         clientConnection: { prompt: promptSpy },
         logWriter: {
+          appendRawLine: vi.fn(),
           flushAll: vi.fn().mockResolvedValue(undefined),
           getFullAgentResponse: vi.fn().mockReturnValue(null),
           resetTurnMessages: vi.fn(),
@@ -535,6 +540,7 @@ describe("Question relay", () => {
         acpSessionId: "acp-session",
         clientConnection: { prompt: promptSpy },
         logWriter: {
+          appendRawLine: vi.fn(),
           flushAll: vi.fn().mockResolvedValue(undefined),
           getFullAgentResponse: vi.fn().mockReturnValue(null),
           resetTurnMessages: vi.fn(),
@@ -551,6 +557,147 @@ describe("Question relay", () => {
       });
     });
 
+    it.each([
+      {
+        name: "marks automation-triggered runs completed after a successful first turn",
+        state: { automation_id: "automation-1" },
+        agentResponse: "At 2026-05-13 17:45, the waitlist count is 2827.",
+        expectCompleted: true,
+      },
+      {
+        name: "keeps non-automation runs open after a successful first turn",
+        state: {},
+        agentResponse: "done",
+        expectCompleted: false,
+      },
+    ])("$name", async ({ state, agentResponse, expectCompleted }) => {
+      vi.spyOn(server.posthogAPI, "getTask").mockResolvedValue({
+        id: "test-task-id",
+        title: "t",
+        description: "original task description",
+      } as unknown as Task);
+      vi.spyOn(server.posthogAPI, "getTaskRun").mockResolvedValue({
+        id: "test-run-id",
+        task: "test-task-id",
+        state,
+      } as unknown as TaskRun);
+      vi.spyOn(server, "syncCloudBranchMetadata").mockResolvedValue(undefined);
+
+      const promptSpy = vi.fn().mockResolvedValue({ stopReason: "end_turn" });
+      const updateTaskRunSpy = vi
+        .spyOn(server.posthogAPI, "updateTaskRun")
+        .mockResolvedValue({} as TaskRun);
+      const relaySpy = vi
+        .spyOn(server.posthogAPI, "relayMessage")
+        .mockResolvedValue(undefined);
+      server.session = {
+        payload: TEST_PAYLOAD,
+        acpSessionId: "acp-session",
+        clientConnection: { prompt: promptSpy },
+        logWriter: {
+          appendRawLine: vi.fn(),
+          flushAll: vi.fn().mockResolvedValue(undefined),
+          getFullAgentResponse: vi.fn().mockReturnValue(agentResponse),
+          resetTurnMessages: vi.fn(),
+          flush: vi.fn().mockResolvedValue(undefined),
+          isRegistered: vi.fn().mockReturnValue(true),
+        },
+      };
+
+      await server.sendInitialTaskMessage(TEST_PAYLOAD);
+
+      expect(relaySpy).toHaveBeenCalledWith(
+        "test-task-id",
+        "test-run-id",
+        agentResponse,
+      );
+
+      if (expectCompleted) {
+        expect(updateTaskRunSpy).toHaveBeenCalledWith(
+          "test-task-id",
+          "test-run-id",
+          {
+            status: "completed",
+          },
+        );
+      } else {
+        expect(updateTaskRunSpy).not.toHaveBeenCalledWith(
+          "test-task-id",
+          "test-run-id",
+          {
+            status: "completed",
+          },
+        );
+      }
+    });
+
+    it("marks automation-triggered runs completed after a successful resume turn", async () => {
+      vi.spyOn(server.posthogAPI, "getTaskRun").mockResolvedValue({
+        id: "test-run-id",
+        task: "test-task-id",
+        state: { automation_id: "automation-1" },
+      } as unknown as TaskRun);
+      vi.spyOn(server, "syncCloudBranchMetadata").mockResolvedValue(undefined);
+
+      const promptSpy = vi.fn().mockResolvedValue({ stopReason: "end_turn" });
+      const updateTaskRunSpy = vi
+        .spyOn(server.posthogAPI, "updateTaskRun")
+        .mockResolvedValue({} as TaskRun);
+      const relaySpy = vi
+        .spyOn(server.posthogAPI, "relayMessage")
+        .mockResolvedValue(undefined);
+      server.resumeState = {
+        conversation: [
+          {
+            role: "user",
+            content: [{ type: "text", text: "Please continue from here." }],
+          },
+        ],
+        latestGitCheckpoint: null,
+        interrupted: false,
+        logEntryCount: 1,
+      };
+      server.session = {
+        payload: TEST_PAYLOAD,
+        acpSessionId: "acp-session",
+        clientConnection: { prompt: promptSpy },
+        logWriter: {
+          appendRawLine: vi.fn(),
+          flushAll: vi.fn().mockResolvedValue(undefined),
+          getFullAgentResponse: vi.fn().mockReturnValue("resume reply"),
+          resetTurnMessages: vi.fn(),
+          flush: vi.fn().mockResolvedValue(undefined),
+          isRegistered: vi.fn().mockReturnValue(true),
+        },
+      };
+
+      await server.sendInitialTaskMessage(TEST_PAYLOAD);
+
+      expect(promptSpy).toHaveBeenCalledWith({
+        sessionId: "acp-session",
+        prompt: [
+          expect.objectContaining({
+            type: "text",
+            text: expect.stringContaining(
+              "You are resuming a previous conversation.",
+            ),
+          }),
+        ],
+      });
+      expect(relaySpy).toHaveBeenCalledWith(
+        "test-task-id",
+        "test-run-id",
+        "resume reply",
+      );
+      expect(updateTaskRunSpy).toHaveBeenCalledWith(
+        "test-task-id",
+        "test-run-id",
+        {
+          status: "completed",
+        },
+      );
+    });
+
     it("does not replay a transient upstream termination before any session activity", async () => {
       vi.spyOn(server.posthogAPI, "getTask").mockResolvedValue({
         id: "test-task-id",