diff --git a/router/deployment_router.go b/router/deployment_router.go
index a220b89..5beda83 100644
--- a/router/deployment_router.go
+++ b/router/deployment_router.go
@@ -146,8 +146,12 @@ func (r *DeploymentRouter) Chat(ctx context.Context, messages []client.EyrieMess
 		if attempts < 1 {
 			attempts = 1
 		}
+		// Track the deployment that just failed this stage so the next attempt
+		// prefers a different deployment when one is available, instead of
+		// re-selecting the same dead endpoint up to stage.Retries times.
+		recentlyFailed := ""
 		for attempt := 0; attempt < attempts; attempt++ {
-			choice := selectDeploymentChoice(choices)
+			choice := selectDeploymentChoice(choices, recentlyFailed)
 			resp, err := r.chatWithDeployment(ctx, messages, opts, target, choice.DeploymentID)
 			if err == nil {
 				r.recordSuccess(choice.DeploymentID)
@@ -161,6 +165,7 @@ func (r *DeploymentRouter) Chat(ctx context.Context, messages []client.EyrieMess
 				}
 				return nil, err
 			}
+			recentlyFailed = choice.DeploymentID
 		}
 	}
 	if lastErr == nil {
@@ -189,8 +194,12 @@ func (r *DeploymentRouter) StreamChat(ctx context.Context, messages []client.Eyr
 			if attempts < 1 {
 				attempts = 1
 			}
+			// Prefer a different deployment than the one that just failed
+			// this stage, instead of re-selecting the same dead endpoint
+			// up to stage.Retries times.
+			recentlyFailed := ""
 			for attempt := 0; attempt < attempts; attempt++ {
-				choice := selectDeploymentChoice(choices)
+				choice := selectDeploymentChoice(choices, recentlyFailed)
 				fallback, err := r.streamWithDeployment(streamCtx, out, messages, opts, target, choice.DeploymentID)
 				if err == nil {
 					r.recordSuccess(choice.DeploymentID)
@@ -215,6 +224,7 @@ func (r *DeploymentRouter) StreamChat(ctx context.Context, messages []client.Eyr
 					}
 					return
 				}
+				recentlyFailed = choice.DeploymentID
 			}
 		}
 		if lastErr == nil {
@@ -560,25 +570,41 @@ func offeringSupportsTools(offering catalog.ModelOffering, tools []string) bool
 	return true
 }
 
-func selectDeploymentChoice(choices []DeploymentChoice) DeploymentChoice {
+// selectDeploymentChoice picks a deployment from choices using weighted random
+// selection. The deployment whose ID equals exclude is skipped when more than
+// one option is available, so a retry after a failure prefers a different
+// endpoint instead of hammering the same dead one.
+func selectDeploymentChoice(choices []DeploymentChoice, exclude string) DeploymentChoice {
 	if len(choices) == 1 {
 		return choices[0]
 	}
+	alternatives := choices
+	if exclude != "" {
+		filtered := make([]DeploymentChoice, 0, len(choices))
+		for _, c := range choices {
+			if c.DeploymentID != exclude {
+				filtered = append(filtered, c)
+			}
+		}
+		if len(filtered) > 0 {
+			alternatives = filtered
+		}
+	}
 	total := 0
-	for _, choice := range choices {
+	for _, choice := range alternatives {
 		total += choice.Weight
 	}
 	if total <= 0 {
-		return choices[0]
+		return alternatives[0]
 	}
 	n := rand.IntN(total) // #nosec G404 -- non-cryptographic weighted load-balancing choice, not a security decision
-	for _, choice := range choices {
+	for _, choice := range alternatives {
 		n -= choice.Weight
 		if n < 0 {
 			return choice
 		}
 	}
-	return choices[len(choices)-1]
+	return alternatives[len(alternatives)-1]
 }
 
 func isOutputEvent(event client.EyrieStreamEvent) bool {
diff --git a/router/deployment_router_test.go b/router/deployment_router_test.go
index 9d89c20..d29b117 100644
--- a/router/deployment_router_test.go
+++ b/router/deployment_router_test.go
@@ -16,11 +16,13 @@ type deploymentMockProvider struct {
 	lastModel  string
 	lastTools  []client.EyrieTool
 	streamDone bool
+	callCount  int
 }
 
 func (m *deploymentMockProvider) Chat(_ context.Context, _ []client.EyrieMessage, opts client.ChatOptions) (*client.EyrieResponse, error) {
 	m.lastModel = opts.Model
 	m.lastTools = opts.Tools
+	m.callCount++
 	if m.err != nil {
 		return nil, m.err
 	}
@@ -360,3 +362,50 @@ func TestDeploymentRouterNativeMimoUsesConfiguredXiaomiDeployment(t *testing.T)
 		t.Fatalf("native model = %q", mimo.lastModel)
 	}
 }
+
+// TestDeploymentRouterRetriesPreferDifferentEndpoint verifies the fix for
+// "deployment retry can re-select the same dead deployment": when a stage
+// has multiple deployments and the first choice fails transiently, the next
+// attempt should prefer a different deployment (and the healthy one is
+// reached) instead of retrying the same dead endpoint up to stage.Retries.
+func TestDeploymentRouterRetriesPreferDifferentEndpoint(t *testing.T) {
+	t.Parallel()
+	dead := &deploymentMockProvider{name: "direct", err: fmt.Errorf("HTTP 503 unavailable")}
+	healthy := &deploymentMockProvider{name: "vertex"}
+	r, err := NewDeploymentRouter(DeploymentRouterOptions{
+		Catalog: testCompiledCatalog(t),
+		Deployments: map[string]DeploymentAdapter{
+			"anthropic-direct": {Provider: dead},
+			"anthropic-vertex": {Provider: healthy},
+		},
+		Routing: RoutingPolicy{Providers: map[string][]RoutingStage{"anthropic": {{
+			Deployments: []DeploymentChoice{
+				{DeploymentID: "anthropic-direct", Weight: 100},
+				{DeploymentID: "anthropic-vertex", Weight: 1},
+			},
+			Retries: 3,
+		}}}},
+	})
+	if err != nil {
+		t.Fatal(err)
+	}
+
+	resp, err := r.Chat(context.Background(),
+		[]client.EyrieMessage{{Role: "user", Content: "hi"}},
+		client.ChatOptions{Model: "anthropic/claude-sonnet-4-6"})
+	if err != nil {
+		t.Fatalf("Chat: %v", err)
+	}
+	if resp.Content != "from vertex" {
+		t.Fatalf("expected vertex (healthy) deployment after direct (dead) failed, got %q", resp.Content)
+	}
+	// The dead provider is tried at most once (to discover the failure); the
+	// retry must prefer the healthy endpoint instead of re-selecting the same
+	// dead one up to stage.Retries times.
+	if dead.callCount > 1 {
+		t.Fatalf("dead deployment retried %d times; want at most 1", dead.callCount)
+	}
+	if healthy.callCount != 1 {
+		t.Fatalf("healthy deployment called %d times; want 1", healthy.callCount)
+	}
+}