diff --git a/apps/web/src/features/block-md/definition.ts b/apps/web/src/features/block-md/definition.ts
index 5656d60edcc..f36dbc2cab1 100644
--- a/apps/web/src/features/block-md/definition.ts
+++ b/apps/web/src/features/block-md/definition.ts
@@ -53,6 +53,9 @@ export const definition = defineBlock({
         registerDocumentSpan(documentId, rootSpan);
       }
       return rootSpan.span('doc.load', async (loadSpan) => {
+        // The long-lived root may not be retained, so keep completed loads
+        // independently searchable by document.
+        loadSpan.setAttr('document.id', documentId);
         const loadBundle = () =>
           loadSpan.span('doc.load.bundle', async (bundleSpan) => {
             const result = await fetchDocumentLoadBundle(documentId);
diff --git a/packages/observability/src/span.ts b/packages/observability/src/span.ts
index 366e37ab7a5..7a0acc8c3a0 100644
--- a/packages/observability/src/span.ts
+++ b/packages/observability/src/span.ts
@@ -99,10 +99,26 @@ export class SpanImpl implements Span {
 	}
 
 	private static normalizeError(error: unknown): Error | string {
-		return error instanceof Error ||
-			typeof error === "string" ||
-			(typeof error === "object" && error !== null && "message" in error)
-			? (error as Error | string)
-			: String(error);
+		if (error instanceof Error || typeof error === "string") return error;
+
+		if (
+			typeof error === "object" &&
+			error !== null &&
+			"message" in error &&
+			typeof error.message === "string"
+		) {
+			return new Error(error.message);
+		}
+
+		if (typeof error === "object" && error !== null) {
+			try {
+				const message = JSON.stringify(error);
+				if (message !== undefined) return new Error(message);
+			} catch {
+				return new Error("Unserializable thrown object");
+			}
+		}
+
+		return new Error(String(error));
 	}
 }
diff --git a/packages/observability/src/telemetry.test.ts b/packages/observability/src/telemetry.test.ts
index 65820b54f3c..055b45bbbf4 100644
--- a/packages/observability/src/telemetry.test.ts
+++ b/packages/observability/src/telemetry.test.ts
@@ -172,6 +172,20 @@ describe("Telemetry", () => {
 		expect(exported?.events[0]?.name).toBe("exception");
 	});
 
+	test("records structured non-Error values", () => {
+		const span = Telemetry.span("edit.apply");
+		span.error([{ code: "ImportFailed", detail: "missing dependency" }]);
+		span.end();
+
+		const [exported] = spanExporter.getFinishedSpans();
+		expect(exported?.status.message).toBe(
+			'[{"code":"ImportFailed","detail":"missing dependency"}]',
+		);
+		expect(exported?.events[0]?.attributes?.["exception.message"]).toBe(
+			'[{"code":"ImportFailed","detail":"missing dependency"}]',
+		);
+	});
+
 	test("emits structured logs", () => {
 		Telemetry.warn("WAL flush not acked", {
 			"document.id": "doc-1",
diff --git a/services/sync-service/wrangler.docker.toml b/services/sync-service/wrangler.docker.toml
index 68c13429603..845cb99b4a4 100644
--- a/services/sync-service/wrangler.docker.toml
+++ b/services/sync-service/wrangler.docker.toml
@@ -95,7 +95,7 @@ name = "sync-service-prod2"
 
 [env.prod.vars]
 INTERNAL_API_SECRET_KEY = "SYNC_SERVICE_KEY_PROD"
-ENVIRONMENT = "production"
+ENVIRONMENT = "prod"
 SPS_URL = "https://search-processing.macro.com"
 
 [env.prod.durable_objects]
diff --git a/services/sync-service/wrangler.toml b/services/sync-service/wrangler.toml
index f80ba658cd5..ff7c8a1894c 100644
--- a/services/sync-service/wrangler.toml
+++ b/services/sync-service/wrangler.toml
@@ -3,7 +3,7 @@ main = "build/worker/shim.mjs"
 compatibility_date = "2025-03-05"
 
 [build]
-command = "cargo install -q worker-build@0.8.4 --locked && worker-build --profile sync-service-release"
+command = "cargo install -q worker-build@0.8.4 --locked --force && worker-build --profile sync-service-release"
 
 [observability.logs]
 enabled = true
@@ -138,7 +138,7 @@ name = "sync-service-prod2"
 
 [env.prod.vars]
 INTERNAL_API_SECRET_KEY = "SYNC_SERVICE_KEY_PROD"
-ENVIRONMENT = "production"
+ENVIRONMENT = "prod"
 # The proxy injects the Datadog key; the exporter appends the signal path.
 OTEL_EXPORTER_OTLP_ENDPOINT = "https://macro-prox-prod.macroverse.workers.dev/i/otlp"
 SPS_URL = "https://search-processing.macro.com"