diff --git a/src/engine.ts b/src/engine.ts
index 1aabd84..35b2950 100644
--- a/src/engine.ts
+++ b/src/engine.ts
@@ -3,6 +3,7 @@ import { exec } from "@actions/exec";
 import { dump, load } from "js-yaml";
 import type { ComposeSpec } from "./compose.js";
 import type { Settings } from "./settings.js";
+import type { TaskInfo } from "./types.js";
 import { mapToObject } from "./utils";
 
 /**
@@ -274,6 +275,30 @@ export async function getServiceLogs(
   }
 }
 
+/**
+ * List tasks for a service
+ *
+ * This function retrieves the list of tasks for a service, which includes
+ * information about task states, errors, and failure reasons.
+ *
+ * @param serviceId The ID or name of the service
+ * @returns Array of task information objects
+ */
+export async function listServiceTasks(serviceId: string) {
+  try {
+    const output = await executeDockerCommand(
+      ["service", "ps", "--format=json", "--no-trunc", serviceId],
+      { silent: true },
+    );
+
+    return parseLineDelimitedJson<TaskInfo>(output);
+  } catch (cause) {
+    throw new Error(`Failed to list tasks for service "${serviceId}": ${cause}`, {
+      cause,
+    });
+  }
+}
+
 export async function listSecrets(filters: {
   id?: ValueFilter;
   name?: ValueFilter;
diff --git a/src/monitoring.ts b/src/monitoring.ts
index 010ce74..b633648 100644
--- a/src/monitoring.ts
+++ b/src/monitoring.ts
@@ -2,10 +2,12 @@ import * as core from "@actions/core";
 import {
   getServiceLogs,
   listServices,
+  listServiceTasks,
   type Service,
   type ServiceWithMetadata,
 } from "./engine.js";
 import type { Settings } from "./settings.js";
+import type { TaskInfo } from "./types.js";
 import { sleep } from "./utils.js";
 
 /**
@@ -63,20 +65,48 @@ export async function monitorDeployment(settings: Readonly<Settings>) {
       try {
         complete = isServiceUpdateComplete(service);
       } catch (error) {
-        const logs = await getServiceLogs(service.ID, { since: startTime });
         const message = error instanceof Error ? error.message : String(error);
 
-        core.error(
-          new Error(
-            `Service "${serviceIdentifier}" failed to update: ${message}`,
-            { cause: error },
-          ),
-        );
-        core.error(`Service Details:\n${JSON.stringify(service, null, 2)}`);
+        // Fetch task details to get actionable error information
+        let taskFailureDetails: string | undefined;
+        try {
+          const tasks = await listServiceTasks(service.ID);
+          taskFailureDetails = await getTaskFailureDetails(tasks);
+        } catch (taskError) {
+          core.debug(
+            `Failed to fetch task details: ${taskError instanceof Error ? taskError.message : String(taskError)}`,
+          );
+        }
+
+        // Build comprehensive error message with task details
+        const errorMessage = taskFailureDetails
+          ? `Service "${serviceIdentifier}" failed to update: ${message}. ${taskFailureDetails}`
+          : `Service "${serviceIdentifier}" failed to update: ${message}`;
+
+        // Single error annotation with actionable information
+        core.error(new Error(errorMessage, { cause: error }));
+
+        // Fetch logs for summary
+        const logs = await getServiceLogs(service.ID, { since: startTime });
         core.setOutput("service-logs", logs.toString());
-        core.summary.addHeading("Service Logs", 2);
+
+        // Add detailed information to job summary (not as error annotation)
+        core.summary.addHeading("Service Update Failure Details", 2);
         core.summary.addRaw(
-          `Before the "${serviceIdentifier}" service update failed, the following logs were generated:`,
+          `Service "${serviceIdentifier}" failed to update.`,
+          true,
+        );
+
+        // Add task failure details to summary if available
+        if (taskFailureDetails) {
+          core.summary.addHeading("Task Failure Reason", 3);
+          core.summary.addRaw(taskFailureDetails, true);
+        }
+
+        // Add service logs to summary
+        core.summary.addHeading("Service Logs", 3);
+        core.summary.addRaw(
+          `Logs generated before the service update failed:`,
           true,
         );
         core.summary.addTable([
@@ -99,6 +129,10 @@ export async function monitorDeployment(settings: Readonly<Settings>) {
           ]),
         ]);
 
+        // Add service details to summary for debugging
+        core.summary.addHeading("Service Details (Debug)", 3);
+        core.summary.addCodeBlock(JSON.stringify(service, null, 2), "json");
+
         throw error;
       }
 
@@ -240,12 +274,66 @@ function resolveFailureReason(
 ) {
   const reason =
     {
-      paused: "Service is paused",
+      paused:
+        "Service update paused due to task failure (check task logs for details)",
       rollback_started: "Service failed to update and is being rolled back",
       rollback_completed: "Service failed to update and was rolled back",
-      rollback_paused: "Service is paused and is being rolled back",
+      rollback_paused:
+        "Service rollback paused due to task failure (check task logs for details)",
       unknown: `Service update status '${state}' is unknown`,
     }[state] ?? "Unknown failure reason";
 
   return reason + (message ? `: ${message}` : "");
 }
+
+/**
+ * Extract actionable error information from failed tasks
+ *
+ * This function analyzes failed tasks to provide meaningful error messages
+ * that help diagnose why a service update failed. It examines task states,
+ * error messages, and failure patterns to give actionable feedback.
+ *
+ * @param tasks Array of tasks from docker service ps
+ * @returns A string describing the task failure reason, or undefined if no clear failure
+ */
+async function getTaskFailureDetails(
+  tasks: TaskInfo[],
+): Promise<string | undefined> {
+  // Filter to only failed or rejected tasks
+  const failedTasks = tasks.filter(
+    (task) =>
+      task.Status.State === "failed" ||
+      task.Status.State === "rejected" ||
+      task.DesiredState === "shutdown",
+  );
+
+  if (failedTasks.length === 0) {
+    return undefined;
+  }
+
+  // Get the most recent failed task
+  const recentFailedTask = failedTasks.sort(
+    (a, b) =>
+      new Date(b.UpdatedAt).getTime() - new Date(a.UpdatedAt).getTime(),
+  )[0];
+
+  // Extract error information
+  const errorParts: string[] = [];
+
+  if (recentFailedTask.Status.Err) {
+    errorParts.push(recentFailedTask.Status.Err);
+  } else if (recentFailedTask.Status.Message) {
+    errorParts.push(recentFailedTask.Status.Message);
+  }
+
+  // Add context about the task state
+  if (recentFailedTask.Status.State === "rejected") {
+    errorParts.push("task was rejected by the scheduler");
+  } else if (recentFailedTask.Status.State === "failed") {
+    errorParts.push("task failed to start or run successfully");
+  }
+
+  return errorParts.length > 0
+    ? `Task ${recentFailedTask.ID.substring(0, 12)} ${errorParts.join(": ")}`
+    : undefined;
+}
diff --git a/tests/engine.test.ts b/tests/engine.test.ts
index 07edcd6..792d74b 100644
--- a/tests/engine.test.ts
+++ b/tests/engine.test.ts
@@ -455,6 +455,67 @@ services:
     });
   });
 
+  describe("listServiceTasks", () => {
+    it("should list tasks for a service", async () => {
+      const mockTasks = [
+        {
+          ID: "task1abc",
+          ServiceID: "service123",
+          NodeID: "node1",
+          DesiredState: "running",
+          Status: { State: "running" },
+          CreatedAt: "2024-01-01T00:00:00Z",
+          UpdatedAt: "2024-01-01T00:00:01Z",
+        },
+        {
+          ID: "task2def",
+          ServiceID: "service123",
+          NodeID: "node1",
+          DesiredState: "shutdown",
+          Status: { State: "failed", Err: "container exited with code 1" },
+          CreatedAt: "2024-01-01T00:00:00Z",
+          UpdatedAt: "2024-01-01T00:00:02Z",
+        },
+      ];
+      const mockOutput = mockTasks.map((t) => JSON.stringify(t)).join("\n");
+      
+      mockedExec.mockImplementation(async (_0, _1, options) => {
+        options?.listeners?.stdout?.(Buffer.from(mockOutput));
+        return 0;
+      });
+
+      const tasks = await engine.listServiceTasks("service123");
+
+      expect(mockedExec).toHaveBeenCalledWith(
+        "docker",
+        ["service", "ps", "--format=json", "--no-trunc", "service123"],
+        expect.objectContaining({ silent: true }),
+      );
+      expect(tasks).toHaveLength(2);
+      expect(tasks[0].ID).toBe("task1abc");
+      expect(tasks[1].Status.Err).toBe("container exited with code 1");
+    });
+
+    it("should handle empty task list", async () => {
+      mockedExec.mockImplementation(async (_0, _1, options) => {
+        options?.listeners?.stdout?.(Buffer.from(""));
+        return 0;
+      });
+
+      const tasks = await engine.listServiceTasks("service123");
+
+      expect(tasks).toHaveLength(0);
+    });
+
+    it("should throw error on exec failure", async () => {
+      mockedExec.mockRejectedValue(new Error("Docker error"));
+      
+      await expect(engine.listServiceTasks("service123")).rejects.toThrowError(
+        /Failed to list tasks for service/,
+      );
+    });
+  });
+
   describe("listSecrets", () => {
     it("should list secrets and parse labels", async () => {
       const mockSecret = {
diff --git a/tests/monitoring.test.ts b/tests/monitoring.test.ts
index 5ab7df9..1177d3c 100644
--- a/tests/monitoring.test.ts
+++ b/tests/monitoring.test.ts
@@ -438,6 +438,81 @@ describe("Monitoring", () => {
     );
   });
 
+  it("should include task failure details in error message", async () => {
+    vi.useFakeTimers();
+
+    const mockTasks = [
+      {
+        ID: "task1abcdefghijklmnop",
+        ServiceID: "web_service",
+        NodeID: "node1",
+        DesiredState: "shutdown",
+        Labels: {},
+        Status: {
+          State: "failed",
+          Err: "task: non-zero exit (1)",
+          Message: "started",
+        },
+        Spec: {},
+        CreatedAt: "2024-01-01T00:00:00Z",
+        UpdatedAt: "2024-01-01T00:00:02Z",
+      },
+    ];
+
+    const serviceHistory = [
+      [
+        {
+          ID: "web_service",
+          Spec: { Name: "test" },
+          UpdateStatus: { State: "paused", Message: "update paused" },
+        } as ServiceWithMetadata,
+      ],
+    ];
+
+    vi.spyOn(engine, "listServices")
+      .mockResolvedValueOnce(serviceHistory[0]);
+    vi.spyOn(engine, "listServiceTasks").mockResolvedValueOnce(mockTasks);
+    vi.spyOn(engine, "getServiceLogs").mockResolvedValueOnce([]);
+
+    // Should include task details in error
+    // noinspection JSVoidFunctionReturnValueUsed
+    const promise = expect(monitorDeployment(settings)).rejects.toThrow();
+    await vi.runAllTimersAsync();
+    await promise;
+
+    // Verify listServiceTasks was called to fetch task details
+    expect(engine.listServiceTasks).toHaveBeenCalledWith("web_service");
+  });
+
+  it("should handle task fetch errors gracefully", async () => {
+    vi.useFakeTimers();
+
+    const serviceHistory = [
+      [
+        {
+          ID: "web_service",
+          Spec: { Name: "test" },
+          UpdateStatus: { State: "paused" },
+        } as ServiceWithMetadata,
+      ],
+    ];
+
+    vi.spyOn(engine, "listServices")
+      .mockResolvedValueOnce(serviceHistory[0]);
+    vi.spyOn(engine, "listServiceTasks").mockRejectedValueOnce(
+      new Error("Failed to fetch tasks"),
+    );
+    vi.spyOn(engine, "getServiceLogs").mockResolvedValueOnce([]);
+
+    // Should still throw error even if task fetch fails
+    // noinspection JSVoidFunctionReturnValueUsed
+    const promise = expect(monitorDeployment(settings)).rejects.toThrowError();
+    await vi.runAllTimersAsync();
+    await promise;
+
+    expect(engine.listServiceTasks).toHaveBeenCalled();
+  });
+
   it("should not monitor deployment if `monitor` is false", async () => {
     vi.spyOn(engine, "listServices");