diff --git a/internal/app/integrations.go b/internal/app/integrations.go
index e0f6d12..8d3302a 100644
--- a/internal/app/integrations.go
+++ b/internal/app/integrations.go
@@ -67,6 +67,53 @@ func (a *App) ensureCaddyRoute(ctx context.Context, p Project) error {
 		"match":  []any{map[string]any{"host": []string{p.RouteHost}}},
 		"handle": []any{map[string]any{"handler": "reverse_proxy", "upstreams": []any{map[string]any{"dial": "unix/" + socketPath}}}},
 	}
+
+	cfg, err := a.fetchCaddyConfig(ctx)
+	if err != nil {
+		return err
+	}
+	indexes := findCaddyRouteIndexesByID(cfg, a.cfg.CaddyServerID, route["@id"].(string))
+	if len(indexes) > 0 {
+		// Update first matching route in place.
+		if err := a.putCaddyRouteAtIndex(ctx, indexes[0], route); err != nil {
+			return err
+		}
+		// Remove stale duplicates from highest index to lowest.
+		for i := len(indexes) - 1; i >= 1; i-- {
+			if err := a.deleteCaddyRouteAtIndex(ctx, indexes[i]); err != nil {
+				return err
+			}
+		}
+		return nil
+	}
+
+	if err := a.appendCaddyRoute(ctx, route); err != nil {
+		// If duplicate race happened, retry once through dedupe/update path.
+		if strings.Contains(err.Error(), "duplicate ID") {
+			cfg2, ferr := a.fetchCaddyConfig(ctx)
+			if ferr != nil {
+				return err
+			}
+			indexes2 := findCaddyRouteIndexesByID(cfg2, a.cfg.CaddyServerID, route["@id"].(string))
+			if len(indexes2) == 0 {
+				return err
+			}
+			if uerr := a.putCaddyRouteAtIndex(ctx, indexes2[0], route); uerr != nil {
+				return uerr
+			}
+			for i := len(indexes2) - 1; i >= 1; i-- {
+				if derr := a.deleteCaddyRouteAtIndex(ctx, indexes2[i]); derr != nil {
+					return derr
+				}
+			}
+			return nil
+		}
+		return err
+	}
+	return nil
+}
+
+func (a *App) appendCaddyRoute(ctx context.Context, route map[string]any) error {
 	body, _ := json.Marshal(route)
 	url := fmt.Sprintf("%s/config/apps/http/servers/%s/routes", a.cfg.CaddyAdminURL, a.cfg.CaddyServerID)
 	req, err := http.NewRequestWithContext(ctx, http.MethodPost, url, strings.NewReader(string(body)))
@@ -86,6 +133,78 @@ func (a *App) ensureCaddyRoute(ctx context.Context, p Project) error {
 	return nil
 }
 
+func (a *App) putCaddyRouteAtIndex(ctx context.Context, idx int, route map[string]any) error {
+	body, _ := json.Marshal(route)
+	url := fmt.Sprintf("%s/config/apps/http/servers/%s/routes/%d", a.cfg.CaddyAdminURL, a.cfg.CaddyServerID, idx)
+	req, err := http.NewRequestWithContext(ctx, http.MethodPut, url, strings.NewReader(string(body)))
+	if err != nil {
+		return err
+	}
+	req.Header.Set("Content-Type", "application/json")
+	resp, err := http.DefaultClient.Do(req)
+	if err != nil {
+		return fmt.Errorf("caddy update request failed: %w", err)
+	}
+	defer resp.Body.Close()
+	if resp.StatusCode >= 300 {
+		respBody, _ := io.ReadAll(resp.Body)
+		return fmt.Errorf("caddy update error: status=%d body=%s", resp.StatusCode, string(respBody))
+	}
+	return nil
+}
+
+func (a *App) deleteCaddyRouteAtIndex(ctx context.Context, idx int) error {
+	url := fmt.Sprintf("%s/config/apps/http/servers/%s/routes/%d", a.cfg.CaddyAdminURL, a.cfg.CaddyServerID, idx)
+	req, err := http.NewRequestWithContext(ctx, http.MethodDelete, url, nil)
+	if err != nil {
+		return err
+	}
+	resp, err := http.DefaultClient.Do(req)
+	if err != nil {
+		return fmt.Errorf("caddy delete request failed: %w", err)
+	}
+	defer resp.Body.Close()
+	if resp.StatusCode >= 300 {
+		respBody, _ := io.ReadAll(resp.Body)
+		return fmt.Errorf("caddy delete error: status=%d body=%s", resp.StatusCode, string(respBody))
+	}
+	return nil
+}
+
+func findCaddyRouteIndexesByID(cfg map[string]any, serverID, routeID string) []int {
+	var out []int
+	apps, ok := cfg["apps"].(map[string]any)
+	if !ok {
+		return out
+	}
+	httpApp, ok := apps["http"].(map[string]any)
+	if !ok {
+		return out
+	}
+	servers, ok := httpApp["servers"].(map[string]any)
+	if !ok {
+		return out
+	}
+	server, ok := servers[serverID].(map[string]any)
+	if !ok {
+		return out
+	}
+	routes, ok := server["routes"].([]any)
+	if !ok {
+		return out
+	}
+	for i, r := range routes {
+		rm, ok := r.(map[string]any)
+		if !ok {
+			continue
+		}
+		if rid, ok := rm["@id"].(string); ok && rid == routeID {
+			out = append(out, i)
+		}
+	}
+	return out
+}
+
 func (a *App) fetchCaddyConfig(ctx context.Context) (map[string]any, error) {
 	req, err := http.NewRequestWithContext(ctx, http.MethodGet, a.cfg.CaddyAdminURL+"/config/", nil)
 	if err != nil {