diff --git a/ai/worker/docker.go b/ai/worker/docker.go
index 4e16d5d0b..2756ab6fc 100644
--- a/ai/worker/docker.go
+++ b/ai/worker/docker.go
@@ -780,9 +780,26 @@ tickerLoop:
 				return err
 			}
 
+			// If the container is running, we're done.
 			if json.State.Running {
 				break tickerLoop
 			}
+
+			// Fail fast on states that won't become running after startup.
+			if json.State != nil {
+				status := strings.ToLower(json.State.Status)
+				// Consider exited/dead as terminal. "removing" will surface via
+				// inspect error or transition to exited/dead shortly.
+				if status == "exited" || status == "dead" {
+					return fmt.Errorf("container entered terminal state before running: %s (exitCode=%d)", json.State.Status, json.State.ExitCode)
+				}
+				if !json.State.Restarting && json.State.ExitCode != 0 {
+					return fmt.Errorf("container exited before running (status=%s, exitCode=%d)", json.State.Status, json.State.ExitCode)
+				}
+				if !json.State.Restarting && json.State.Error != "" {
+					return fmt.Errorf("container error before running: %s", json.State.Error)
+				}
+			}
 		}
 	}
 
diff --git a/ai/worker/docker_test.go b/ai/worker/docker_test.go
index adb3a33fd..ea9d2f975 100644
--- a/ai/worker/docker_test.go
+++ b/ai/worker/docker_test.go
@@ -1165,6 +1165,63 @@ func TestDockerWaitUntilRunning(t *testing.T) {
 		require.Contains(t, err.Error(), "timed out waiting for managed container")
 		mockDockerClient.AssertExpectations(t)
 	})
+
+	t.Run("FailFastOnExited", func(t *testing.T) {
+		// If the container is immediately exited, we should fail fast instead of waiting.
+		mockDockerClient := new(MockDockerClient)
+		// Always return non-running, exited state
+		mockDockerClient.On("ContainerInspect", mock.Anything, containerID).Return(types.ContainerJSON{
+			ContainerJSONBase: &types.ContainerJSONBase{
+				State: &types.ContainerState{
+					Status:   "exited",
+					Running:  false,
+					ExitCode: 137,
+				},
+			},
+		}, nil)
+
+		err := dockerWaitUntilRunning(ctx, mockDockerClient, containerID, pollingInterval)
+		require.Error(t, err)
+		require.Contains(t, err.Error(), "terminal state")
+		mockDockerClient.AssertExpectations(t)
+	})
+
+	t.Run("FailFastOnDead", func(t *testing.T) {
+		mockDockerClient := new(MockDockerClient)
+		mockDockerClient.On("ContainerInspect", mock.Anything, containerID).Return(types.ContainerJSON{
+			ContainerJSONBase: &types.ContainerJSONBase{
+				State: &types.ContainerState{
+					Status:  "dead",
+					Running: false,
+					Error:   "killed",
+				},
+			},
+		}, nil)
+
+		err := dockerWaitUntilRunning(ctx, mockDockerClient, containerID, pollingInterval)
+		require.Error(t, err)
+		require.Contains(t, err.Error(), "container entered terminal state")
+		mockDockerClient.AssertExpectations(t)
+	})
+
+	t.Run("FailFastOnExitCodeNonZeroWithoutRestarting", func(t *testing.T) {
+		mockDockerClient := new(MockDockerClient)
+		mockDockerClient.On("ContainerInspect", mock.Anything, containerID).Return(types.ContainerJSON{
+			ContainerJSONBase: &types.ContainerJSONBase{
+				State: &types.ContainerState{
+					Status:     "created",
+					Running:    false,
+					Restarting: false,
+					ExitCode:   1,
+				},
+			},
+		}, nil)
+
+		err := dockerWaitUntilRunning(ctx, mockDockerClient, containerID, pollingInterval)
+		require.Error(t, err)
+		require.Contains(t, err.Error(), "exited before running")
+		mockDockerClient.AssertExpectations(t)
+	})
 }
 
 func TestHwGPU(t *testing.T) {