diff --git a/PolyPilot.Tests/PermissionDenialDetectionTests.cs b/PolyPilot.Tests/PermissionDenialDetectionTests.cs
index 7fc5057440..bddab3e222 100644
--- a/PolyPilot.Tests/PermissionDenialDetectionTests.cs
+++ b/PolyPilot.Tests/PermissionDenialDetectionTests.cs
@@ -318,3 +318,89 @@ private static string GetRepoRoot()
         return dir ?? throw new InvalidOperationException("Could not find repo root");
     }
 }
+
+/// <summary>
+/// Tests for CopilotService.IsInitializationError — the helper that detects
+/// "Service not initialized" exceptions so worker dispatch can retry them
+/// with a lazy re-init attempt instead of failing immediately (PR #422).
+/// </summary>
+public class InitializationErrorDetectionTests
+{
+    [Fact]
+    public void IsInitializationError_ServiceNotInitialized_ReturnsTrue()
+    {
+        var ex = new InvalidOperationException("Service not initialized. Call InitializeAsync first.");
+        Assert.True(CopilotService.IsInitializationError(ex));
+    }
+
+    [Fact]
+    public void IsInitializationError_ClientNotInitialized_ReturnsTrue()
+    {
+        var ex = new InvalidOperationException("Client is not initialized");
+        Assert.True(CopilotService.IsInitializationError(ex));
+    }
+
+    [Theory]
+    [InlineData("Service not initialized. Call InitializeAsync first.")]
+    [InlineData("Client is not initialized")]
+    [InlineData("NOT INITIALIZED")]   // case-insensitive
+    public void IsInitializationError_Variants_ReturnsTrue(string message)
+    {
+        var ex = new InvalidOperationException(message);
+        Assert.True(CopilotService.IsInitializationError(ex));
+    }
+
+    [Fact]
+    public void IsInitializationError_ConnectionRefused_ReturnsFalse()
+    {
+        // Connection errors are handled by IsConnectionError, not IsInitializationError
+        var ex = new InvalidOperationException("connection refused");
+        Assert.False(CopilotService.IsInitializationError(ex));
+    }
+
+    [Fact]
+    public void IsInitializationError_WrongExceptionType_ReturnsFalse()
+    {
+        // Only InvalidOperationException matches — not base Exception
+        var ex = new Exception("Service not initialized");
+        Assert.False(CopilotService.IsInitializationError(ex));
+    }
+
+    [Fact]
+    public void IsInitializationError_ArbitraryInvalidOperation_ReturnsFalse()
+    {
+        var ex = new InvalidOperationException("Session 'foo' already exists.");
+        Assert.False(CopilotService.IsInitializationError(ex));
+    }
+
+    [Fact]
+    public void IsInitializationError_HelperIsInternal_CanBeTestedViaPublicSurface()
+    {
+        // The helper is internal — verify it's accessible from tests (InternalsVisibleTo).
+        // Also verify the helper exists in CopilotService.Utilities.cs at the right location.
+        var repoRoot = GetRepoRoot();
+        var source = File.ReadAllText(Path.Combine(repoRoot, "PolyPilot", "Services", "CopilotService.Utilities.cs"));
+        Assert.Contains("internal static bool IsInitializationError(Exception ex)", source);
+        Assert.Contains("not initialized", source);
+    }
+
+    [Fact]
+    public void ExecuteWorkerAsync_RetryGate_IncludesInitializationError()
+    {
+        // Structural: the retry catch in ExecuteWorkerAsync must check IsInitializationError
+        // so "Service not initialized" triggers a retry with lazy re-init, not an immediate fail.
+        var repoRoot = GetRepoRoot();
+        var source = File.ReadAllText(Path.Combine(repoRoot, "PolyPilot", "Services", "CopilotService.Organization.cs"));
+        Assert.Contains("IsInitializationError(ex)", source);
+        // The retry gate must combine both checks
+        Assert.Contains("IsConnectionError(ex) || IsInitializationError(ex)", source);
+    }
+
+    private static string GetRepoRoot()
+    {
+        var dir = AppContext.BaseDirectory;
+        while (dir != null && !File.Exists(Path.Combine(dir, "PolyPilot.slnx")))
+            dir = Path.GetDirectoryName(dir);
+        return dir ?? throw new InvalidOperationException("Could not find repo root");
+    }
+}
diff --git a/PolyPilot/Services/CopilotService.Organization.cs b/PolyPilot/Services/CopilotService.Organization.cs
index 907f85b3ad..2df2e8f7db 100644
--- a/PolyPilot/Services/CopilotService.Organization.cs
+++ b/PolyPilot/Services/CopilotService.Organization.cs
@@ -2247,9 +2247,17 @@ private async Task<WorkerResult> ExecuteWorkerAsync(string workerName, string ta
                 Debug($"[DISPATCH] Worker '{workerName}' completed (response len={response?.Length ?? 0}, elapsed={sw.Elapsed.TotalSeconds:F1}s)");
                 return new WorkerResult(workerName, response, true, null, sw.Elapsed);
             }
-            catch (Exception ex) when (attempt < maxRetries && IsConnectionError(ex))
+            catch (Exception ex) when (attempt < maxRetries && (IsConnectionError(ex) || IsInitializationError(ex)))
             {
                 Debug($"[DISPATCH] Worker '{workerName}' attempt {attempt} failed with {ex.GetType().Name} — retrying in 2s");
+                // If the service became uninitialized (e.g., a concurrent worker's connection
+                // error set IsInitialized=false), attempt lazy re-init before the next try.
+                if (!IsInitialized || _client == null)
+                {
+                    Debug($"[DISPATCH] Worker '{workerName}': service uninitialized — attempting lazy re-init before retry");
+                    try { await InitializeAsync(cancellationToken); }
+                    catch (Exception reinitEx) { Debug($"[DISPATCH] Worker '{workerName}': lazy re-init failed: {reinitEx.Message}"); }
+                }
                 await Task.Delay(2000, cancellationToken);
                 continue;
             }
diff --git a/PolyPilot/Services/CopilotService.Utilities.cs b/PolyPilot/Services/CopilotService.Utilities.cs
index f2b8190ede..541951c990 100644
--- a/PolyPilot/Services/CopilotService.Utilities.cs
+++ b/PolyPilot/Services/CopilotService.Utilities.cs
@@ -470,6 +470,14 @@ internal static bool IsConnectionError(Exception ex)
         return ex.InnerException != null && IsConnectionError(ex.InnerException);
     }
 
+    /// <summary>
+    /// Returns true if the exception indicates the Copilot service is not yet initialized
+    /// (e.g., _client is null after a previous connection failure). These are retryable in
+    /// multi-agent worker dispatch with a lazy re-init attempt before the next retry.
+    /// </summary>
+    internal static bool IsInitializationError(Exception ex) =>
+        ex is InvalidOperationException && ex.Message.Contains("not initialized", StringComparison.OrdinalIgnoreCase);
+
     /// <summary>
     /// Returns true if the exception indicates the CLI server process is dead
     /// (e.g., Process.HasExited throws because the Process handle was never started