diff --git a/command/main.ts b/command/main.ts
index f0da5a1..25ec5a1 100644
--- a/command/main.ts
+++ b/command/main.ts
@@ -22,7 +22,7 @@ import { trust } from "./trust";
 export const main = defineCommand({
   meta: {
     name: "kuber",
-    version: "2.3.2",
+    version: "2.3.3",
     description: "Docker Compose -> K8s translation layer",
   },
   args: {
diff --git a/command/up.ts b/command/up.ts
index ad8b657..2b6efea 100644
--- a/command/up.ts
+++ b/command/up.ts
@@ -1,6 +1,7 @@
 import { defineCommand } from "citty";
 import { Listr, type ListrTaskWrapper } from "listr2";
 import { randomUUID } from "node:crypto";
+import { isDeepStrictEqual } from "node:util";
 import type { ComposeSpecification } from "../schema/docker.d";
 import type { KuberResource } from "../types";
 import {
@@ -29,6 +30,7 @@ import {
 
 type Workspace = {
   metadata: { name: string; uid: string; resourceVersion: string };
+  spec?: { source?: unknown; config?: unknown };
 };
 
 type ResourceIdentity = {
@@ -195,6 +197,27 @@ function workspaceInput(
   };
 }
 
+function workspaceMatchesInput(
+  workspace: Workspace,
+  input: ReturnType<typeof workspaceInput>,
+): boolean {
+  return (
+    isDeepStrictEqual(workspace.spec?.source, input.source) &&
+    isDeepStrictEqual(workspace.spec?.config, input.config)
+  );
+}
+
+function isWorkspaceUpdateAmbiguous(error: unknown): boolean {
+  if (error instanceof KuberApiError) return error.status === 409;
+  if (error instanceof DOMException && error.name === "AbortError")
+    return false;
+  if (error instanceof Error && error.name === "AbortError") return false;
+  return (
+    error instanceof TypeError ||
+    (error instanceof Error && error.name === "TimeoutError")
+  );
+}
+
 export async function ensureWorkspace(
   project: string,
   compose: ComposeSpecification,
@@ -203,21 +226,42 @@ export async function ensureWorkspace(
 ): Promise<Workspace> {
   const path = `/workspaces/${encodeURIComponent(project)}`;
   const input = workspaceInput(compose, snapshot);
+  const update = (workspace: Workspace) =>
+    request<Workspace>(path, {
+      method: "PUT",
+      headers: { "if-match": `"${workspace.metadata.resourceVersion}"` },
+      json: input,
+    });
+  const recover = async (originalError: unknown): Promise<Workspace> => {
+    try {
+      const fresh = await request<Workspace>(path);
+      if (workspaceMatchesInput(fresh, input)) return fresh;
+      return await update(fresh);
+    } catch {
+      throw originalError;
+    }
+  };
   let current: Workspace;
   try {
     current = await request<Workspace>(path);
   } catch (error) {
     if (!(error instanceof KuberApiError) || error.status !== 404) throw error;
-    return request<Workspace>("/workspaces", {
-      method: "POST",
-      json: { id: project, ...input },
-    });
+    try {
+      return await request<Workspace>("/workspaces", {
+        method: "POST",
+        json: { id: project, ...input },
+      });
+    } catch (createError) {
+      if (!isWorkspaceUpdateAmbiguous(createError)) throw createError;
+      return recover(createError);
+    }
+  }
+  try {
+    return await update(current);
+  } catch (updateError) {
+    if (!isWorkspaceUpdateAmbiguous(updateError)) throw updateError;
+    return recover(updateError);
   }
-  return request<Workspace>(path, {
-    method: "PUT",
-    headers: { "if-match": `"${current.metadata.resourceVersion}"` },
-    json: input,
-  });
 }
 
 function operationEnvironment(
diff --git a/package.json b/package.json
index ec5d556..a5b69c8 100644
--- a/package.json
+++ b/package.json
@@ -1,6 +1,6 @@
 {
   "name": "@dmgnr/kuber",
-  "version": "2.3.2",
+  "version": "2.3.3",
   "description": "Docker Compose to Kubernetes translation layer",
   "bin": {
     "kuber": "dist/index.js"
diff --git a/server/app.ts b/server/app.ts
index 8a72db8..90c0710 100644
--- a/server/app.ts
+++ b/server/app.ts
@@ -57,13 +57,14 @@ import {
   WorkspaceConflictError,
   WorkspaceNotFoundError,
   WorkspaceValidationError,
+  WORKSPACE_ID_PATTERN,
   workspaceEtag,
   type CreateWorkspaceInput,
   type UpdateWorkspaceInput,
   type Workspace,
   type WorkspaceStore,
 } from "./workspace-store";
-import { redactString } from "./redact";
+import { REDACTED, redactString } from "./redact";
 
 const API_PREFIX = "/api/v2";
 const RUNTIME_SESSION_MS = 24 * 60 * 60 * 1000;
@@ -107,6 +108,33 @@ export type AppOptions = {
   hashPassword?: (password: string) => Promise<string>;
   now?: () => number;
   requestId?: () => string;
+  logger?: AppLogger;
+};
+
+export type UnknownFailureLog = {
+  event: "request.failed";
+  requestId: string;
+  method: string;
+  pathname: string;
+  workspaceId?: string;
+  status: number;
+  code: string;
+  errorName: string;
+  message: string;
+  kubernetesStatus?: { status?: string; reason?: string; code?: number };
+};
+
+export type RequestErrorLog = Omit<UnknownFailureLog, "event"> & {
+  event: string;
+  operationId?: string;
+};
+
+export interface AppLogger {
+  error(entry: RequestErrorLog): void;
+}
+
+const defaultAppLogger: AppLogger = {
+  error: (entry) => console.error(JSON.stringify(entry)),
 };
 
 type LoginFailures = { count: number; resetAt: number };
@@ -236,6 +264,7 @@ export function createApp(
       Bun.password.hash(password, { algorithm: "argon2id" }));
   const now = options.now ?? Date.now;
   const makeRequestId = options.requestId ?? randomUUID;
+  const logger = options.logger ?? defaultAppLogger;
   const bodyLimit = options.jsonBodyLimit ?? DEFAULT_JSON_LIMIT;
   const allowedOrigins = new Set(options.allowedOrigins ?? []);
   const hasOriginConfiguration = options.allowedOrigins !== undefined;
@@ -282,6 +311,70 @@ export function createApp(
     return result;
   }
 
+  function workspaceIdFromPath(pathname: string): string | undefined {
+    const match = new RegExp(`^${API_PREFIX}/workspaces/([^/]+)`).exec(
+      pathname,
+    );
+    if (!match) return;
+    try {
+      const workspaceId = decodeURIComponent(match[1]!);
+      return WORKSPACE_ID_PATTERN.test(workspaceId) ? workspaceId : undefined;
+    } catch {
+      return;
+    }
+  }
+
+  function kubernetesStatus(
+    error: unknown,
+  ): UnknownFailureLog["kubernetesStatus"] | undefined {
+    if (!isRecord(error)) return;
+    const candidate = isRecord(error.status)
+      ? error.status
+      : isRecord(error.body)
+        ? error.body
+        : undefined;
+    if (!candidate) return;
+    const status = typeof candidate.status === "string" ? REDACTED : undefined;
+    const reason = typeof candidate.reason === "string" ? REDACTED : undefined;
+    const code =
+      typeof candidate.code === "number" ? candidate.code : undefined;
+    return status || reason || code !== undefined
+      ? { status, reason, code }
+      : undefined;
+  }
+
+  function logRequestError(
+    request: Request,
+    error: unknown,
+    {
+      event,
+      code,
+      message,
+      workspaceId,
+      operationId,
+    }: Pick<RequestErrorLog, "event" | "code" | "message"> & {
+      workspaceId?: string;
+      operationId?: string;
+    },
+  ): void {
+    const pathname = new URL(request.url).pathname;
+    logger.error({
+      event,
+      requestId: requestIds.get(request) ?? makeRequestId(),
+      method: request.method,
+      pathname,
+      ...(workspaceId && { workspaceId }),
+      ...(operationId && { operationId }),
+      status: 500,
+      code,
+      errorName: error instanceof Error ? error.name : "UnknownError",
+      message: redactString(message),
+      ...(kubernetesStatus(error) && {
+        kubernetesStatus: kubernetesStatus(error),
+      }),
+    });
+  }
+
   async function readJson(
     request: Request,
     limit = bodyLimit,
@@ -911,10 +1004,13 @@ export function createApp(
             operation.metadata.name,
           );
         } catch (error) {
-          console.error(
-            "Failed to append successful operation audit event",
-            error,
-          );
+          logRequestError(request, error, {
+            event: "operation.audit.failed",
+            code: "AUDIT_APPEND_FAILED",
+            message: "Successful operation audit event could not be appended",
+            workspaceId: workspace.metadata.name,
+            operationId: operation.metadata.name,
+          });
         }
         return response(operationBody(completed, result), 200, {
           location: `${API_PREFIX}/operations/${operation.metadata.name}`,
@@ -948,10 +1044,13 @@ export function createApp(
             operation.metadata.name,
           );
         } catch (auditError) {
-          console.error(
-            "Failed to append failed operation audit event",
-            auditError,
-          );
+          logRequestError(request, auditError, {
+            event: "operation.audit.failed",
+            code: "AUDIT_APPEND_FAILED",
+            message: "Failed operation audit event could not be appended",
+            workspaceId: workspace.metadata.name,
+            operationId: operation.metadata.name,
+          });
         }
         throw new HttpError(
           failureCode === "WORKSPACE_LEASE_LOST" ? 409 : 500,
@@ -968,16 +1067,25 @@ export function createApp(
         try {
           await lease?.release();
         } catch (error) {
-          console.error("Failed to release workspace operation lease", error);
+          logRequestError(request, error, {
+            event: "operation.lease_release.failed",
+            code: "LEASE_RELEASE_FAILED",
+            message: "Workspace operation lease could not be released",
+            workspaceId: workspace.metadata.name,
+            operationId: operation.metadata.name,
+          });
         }
       }
     };
     if (request.headers.get("prefer") === "respond-async") {
       void executeClaimed().catch((error) => {
-        console.error(
-          `Background operation '${operation.metadata.name}' failed`,
-          error,
-        );
+        logRequestError(request, error, {
+          event: "operation.background.failed",
+          code: "BACKGROUND_OPERATION_FAILED",
+          message: "Background operation could not be completed",
+          workspaceId: workspace.metadata.name,
+          operationId: operation.metadata.name,
+        });
       });
       return response(
         {
@@ -2122,7 +2230,6 @@ export function createApp(
       );
     if (error instanceof Error && /already exists/i.test(error.message))
       return new HttpError(409, "Conflict", "ALREADY_EXISTS", error.message);
-    console.error(error);
     return new HttpError(
       500,
       "Internal server error",
@@ -2195,7 +2302,15 @@ export function createApp(
         result = await handleAuthenticated(request, url, identity);
       }
     } catch (error) {
-      result = problem(normalizeError(error), requestId);
+      const normalized = normalizeError(error);
+      if (normalized.code === "INTERNAL_ERROR")
+        logRequestError(request, error, {
+          event: "request.failed",
+          code: normalized.code,
+          message: normalized.message,
+          workspaceId: workspaceIdFromPath(url.pathname),
+        });
+      result = problem(normalized, requestId);
     }
     result.headers.set("x-request-id", requestId);
     if (origin && originAllowed) {
@@ -2220,13 +2335,14 @@ export type ExecConnection = {
 
 export type ExecAuthOptions = Pick<
   AppOptions,
-  "store" | "workspaceStore" | "auditStore" | "now"
+  "store" | "workspaceStore" | "auditStore" | "now" | "logger" | "requestId"
 >;
 
 export async function authorizeExecConnection(
   options: ExecAuthOptions,
   request: Request,
   workspaceId: string,
+  requestId?: string,
 ): Promise<ExecConnection> {
   const now = options.now ?? Date.now;
   const identity = await authenticateRequest(options, request, now);
@@ -2261,7 +2377,22 @@ export async function authorizeExecConnection(
           workspaceId,
         });
       } catch (error) {
-        console.error("Failed to append denied exec audit event", error);
+        const suppliedRequestId = request.headers.get("x-request-id");
+        (options.logger ?? defaultAppLogger).error({
+          event: "exec.audit.failed",
+          requestId:
+            requestId ??
+            (suppliedRequestId && /^[\x21-\x7e]{1,128}$/.test(suppliedRequestId)
+              ? suppliedRequestId
+              : (options.requestId ?? randomUUID)()),
+          method: request.method,
+          pathname: new URL(request.url).pathname,
+          ...(WORKSPACE_ID_PATTERN.test(workspaceId) && { workspaceId }),
+          status: 500,
+          code: "AUDIT_APPEND_FAILED",
+          errorName: error instanceof Error ? error.name : "UnknownError",
+          message: "Denied exec audit event could not be appended",
+        });
       }
     }
     throw new HttpError(
@@ -2289,7 +2420,6 @@ export function execProblem(error: unknown, requestId = ""): Response {
   let httpError: HttpError;
   if (error instanceof HttpError) httpError = error;
   else {
-    console.error(error);
     httpError = new HttpError(
       500,
       "Internal server error",
@@ -2571,11 +2701,33 @@ export async function handleExecUpgrade(
   workspaceId: string,
   upgrade: (request: Request, data: ExecConnection) => boolean,
 ): Promise<Response | undefined> {
+  const suppliedRequestId = request.headers.get("x-request-id");
+  const requestId =
+    suppliedRequestId && /^[\x21-\x7e]{1,128}$/.test(suppliedRequestId)
+      ? suppliedRequestId
+      : (options.requestId ?? randomUUID)();
   let connection: ExecConnection;
   try {
-    connection = await authorizeExecConnection(options, request, workspaceId);
+    connection = await authorizeExecConnection(
+      options,
+      request,
+      workspaceId,
+      requestId,
+    );
   } catch (error) {
-    return execProblem(error);
+    if (!(error instanceof HttpError))
+      (options.logger ?? defaultAppLogger).error({
+        event: "request.failed",
+        requestId,
+        method: request.method,
+        pathname: new URL(request.url).pathname,
+        ...(WORKSPACE_ID_PATTERN.test(workspaceId) && { workspaceId }),
+        status: 500,
+        code: "INTERNAL_ERROR",
+        errorName: error instanceof Error ? error.name : "UnknownError",
+        message: "The request could not be completed",
+      });
+    return execProblem(error, requestId);
   }
   if (!upgrade(request, connection))
     return execProblem(
@@ -2585,6 +2737,7 @@ export async function handleExecUpgrade(
         "UPGRADE_FAILED",
         "WebSocket upgrade failed",
       ),
+      requestId,
     );
   return;
 }
diff --git a/tests/command/up-api.test.ts b/tests/command/up-api.test.ts
index 7f0d7cc..8d17634 100644
--- a/tests/command/up-api.test.ts
+++ b/tests/command/up-api.test.ts
@@ -158,6 +158,163 @@ describe("up API pipeline", () => {
     expect(new Headers(calls[1]?.init?.headers).get("if-match")).toBe('"7"');
   });
 
+  test("retries one conflict using a fresh ETag", async () => {
+    const calls: Array<{ path: string; init?: ApiRequestInit }> = [];
+    let gets = 0;
+    const request: ApiRequester = async <T>(
+      path: string,
+      init?: ApiRequestInit,
+    ) => {
+      calls.push({ path, init });
+      if (!init) {
+        gets += 1;
+        return {
+          metadata: {
+            name: "shop",
+            uid: "uid",
+            resourceVersion: gets === 1 ? "7" : "8",
+          },
+          spec: { source: { uri: "cas://old", digest: "old" }, config: {} },
+        } as T;
+      }
+      if (calls.length === 2)
+        throw new KuberApiError("conflict", 409, {
+          title: "Conflict",
+          status: 409,
+          code: "WORKSPACE_CONFLICT",
+        });
+      return {
+        metadata: { name: "shop", uid: "uid", resourceVersion: "9" },
+      } as T;
+    };
+
+    await ensureWorkspace("shop", { services: {} }, snapshot, request);
+
+    expect(calls.map(({ path }) => path)).toEqual([
+      "/workspaces/shop",
+      "/workspaces/shop",
+      "/workspaces/shop",
+      "/workspaces/shop",
+    ]);
+    expect(new Headers(calls[3]?.init?.headers).get("if-match")).toBe('"8"');
+  });
+
+  test("accepts a fresh workspace that already matches after a conflict", async () => {
+    let gets = 0;
+    let puts = 0;
+    const desired = {
+      source: { uri: `cas://${snapshot.digest}`, digest: snapshot.digest },
+      config: { compose: { services: {} } },
+    };
+    const request: ApiRequester = async <T>(
+      _path: string,
+      init?: ApiRequestInit,
+    ) => {
+      if (!init) {
+        gets += 1;
+        return {
+          metadata: { name: "shop", uid: "uid", resourceVersion: "8" },
+          spec:
+            gets === 1
+              ? { ...desired, source: { uri: "cas://old", digest: "old" } }
+              : desired,
+        } as T;
+      }
+      puts += 1;
+      throw new KuberApiError("conflict", 409, {
+        title: "Conflict",
+        status: 409,
+        code: "WORKSPACE_CONFLICT",
+      });
+    };
+
+    await ensureWorkspace("shop", { services: {} }, snapshot, request);
+
+    expect({ gets, puts }).toEqual({ gets: 2, puts: 1 });
+  });
+
+  test("recovers an ambiguous transport failure after the update committed", async () => {
+    let gets = 0;
+    let puts = 0;
+    const desired = {
+      source: { uri: `cas://${snapshot.digest}`, digest: snapshot.digest },
+      config: { compose: { services: {} } },
+    };
+    const request: ApiRequester = async <T>(
+      _path: string,
+      init?: ApiRequestInit,
+    ) => {
+      if (!init) {
+        gets += 1;
+        return {
+          metadata: { name: "shop", uid: "uid", resourceVersion: "8" },
+          spec:
+            gets === 1
+              ? { ...desired, source: { uri: "cas://old", digest: "old" } }
+              : desired,
+        } as T;
+      }
+      puts += 1;
+      throw new TypeError("connection reset");
+    };
+
+    await ensureWorkspace("shop", { services: {} }, snapshot, request);
+
+    expect({ gets, puts }).toEqual({ gets: 2, puts: 1 });
+  });
+
+  test("recovers an ambiguous transport failure with one fresh-ETag retry", async () => {
+    const etags: string[] = [];
+    let gets = 0;
+    const request: ApiRequester = async <T>(
+      _path: string,
+      init?: ApiRequestInit,
+    ) => {
+      if (!init) {
+        gets += 1;
+        return {
+          metadata: {
+            name: "shop",
+            uid: "uid",
+            resourceVersion: gets === 1 ? "7" : "8",
+          },
+          spec: { source: { uri: "cas://old", digest: "old" }, config: {} },
+        } as T;
+      }
+      etags.push(new Headers(init.headers).get("if-match")!);
+      if (etags.length === 1) throw new TypeError("connection reset");
+      return {
+        metadata: { name: "shop", uid: "uid", resourceVersion: "9" },
+      } as T;
+    };
+
+    await ensureWorkspace("shop", { services: {} }, snapshot, request);
+
+    expect(etags).toEqual(['"7"', '"8"']);
+  });
+
+  test("does not retry a generic workspace update failure", async () => {
+    const failure = new KuberApiError("failed", 500, {
+      title: "Internal server error",
+      status: 500,
+      code: "INTERNAL_ERROR",
+    });
+    let calls = 0;
+    const request: ApiRequester = async <T>() => {
+      calls += 1;
+      if (calls === 1)
+        return {
+          metadata: { name: "shop", uid: "uid", resourceVersion: "7" },
+        } as T;
+      throw failure;
+    };
+
+    await expect(
+      ensureWorkspace("shop", { services: {} }, snapshot, request),
+    ).rejects.toBe(failure);
+    expect(calls).toBe(2);
+  });
+
   test("plans, applies, runs the hook, waits, then deletes stale identities", async () => {
     const order: string[] = [];
     const desired = [
diff --git a/tests/server/app.test.ts b/tests/server/app.test.ts
index 5622687..409e690 100644
--- a/tests/server/app.test.ts
+++ b/tests/server/app.test.ts
@@ -681,6 +681,83 @@ describe("kuber v2 HTTP routes", () => {
     expect(await operationStore.list("demo")).toHaveLength(1);
   });
 
+  test("redacts provider status and reason in correlated generic failure logs", async () => {
+    const workspaceStore = new MemoryWorkspaceStore({
+      uid: () => "workspace-uid",
+    });
+    await workspaceStore.create({
+      id: "demo",
+      source: { uri: "oci://example/demo", digest: "sha256:abc" },
+    });
+    const logs: unknown[] = [];
+    spyOn(workspaceStore, "update").mockRejectedValue(
+      Object.assign(
+        new Error(
+          'provider failed password=top-secret config={"compose":"private"}',
+        ),
+        {
+          name: "KubernetesError",
+          body: {
+            status: "Failure",
+            reason: "InternalError",
+            code: 500,
+            message: "contains top-secret",
+          },
+        },
+      ),
+    );
+    const app = createApp({
+      store: await authenticatedStore("operator"),
+      workspaceStore,
+      requestId: () => "request-123",
+      logger: { error: (entry) => logs.push(entry) },
+    });
+
+    const result = await app(
+      request(
+        "/api/v2/workspaces/demo",
+        {
+          method: "PUT",
+          headers: { "if-match": '"1"' },
+          body: JSON.stringify({
+            source: { uri: "cas://secret-source", digest: "secret-digest" },
+            config: { compose: "private-config", password: "top-secret" },
+          }),
+        },
+        "token",
+      ),
+    );
+
+    expect(result.status).toBe(500);
+    expect(await result.json()).toMatchObject({
+      code: "INTERNAL_ERROR",
+      requestId: "request-123",
+    });
+    expect(logs).toEqual([
+      {
+        event: "request.failed",
+        requestId: "request-123",
+        method: "PUT",
+        pathname: "/api/v2/workspaces/demo",
+        workspaceId: "demo",
+        status: 500,
+        code: "INTERNAL_ERROR",
+        errorName: "KubernetesError",
+        message: "The request could not be completed",
+        kubernetesStatus: {
+          status: "[REDACTED]",
+          reason: "[REDACTED]",
+          code: 500,
+        },
+      },
+    ]);
+    expect(JSON.stringify(logs)).not.toContain("top-secret");
+    expect(JSON.stringify(logs)).not.toContain("private-config");
+    expect(JSON.stringify(logs)).not.toContain("secret-source");
+    expect(JSON.stringify(logs)).not.toContain('"Failure"');
+    expect(JSON.stringify(logs)).not.toContain('"InternalError"');
+  });
+
   test("lists persisted operation events with capability and workspace scope checks", async () => {
     const store = await authenticatedStore("operator");
     const workspaceStore = new MemoryWorkspaceStore({
@@ -801,7 +878,7 @@ describe("kuber v2 HTTP routes", () => {
   });
 
   test("does not expose request internals or corrupt success when auditing fails", async () => {
-    const reported = spyOn(console, "error").mockImplementation(() => {});
+    const logs: unknown[] = [];
     const workspaceStore = new MemoryWorkspaceStore({
       uid: () => "workspace-uid",
     });
@@ -824,6 +901,8 @@ describe("kuber v2 HTTP routes", () => {
         },
         list: async () => [],
       },
+      requestId: () => "audit-request-123",
+      logger: { error: (entry) => logs.push(entry) },
     });
     const result = await app(
       request(
@@ -843,8 +922,23 @@ describe("kuber v2 HTTP routes", () => {
       action: "workspace.stop",
     });
     expect(body.operation.status.state).toBe("succeeded");
-    expect(reported).toHaveBeenCalledTimes(1);
-    reported.mockRestore();
+    expect(logs).toEqual([
+      {
+        event: "operation.audit.failed",
+        requestId: "audit-request-123",
+        method: "POST",
+        pathname: "/api/v2/workspaces/demo/lifecycle",
+        workspaceId: "demo",
+        operationId: "operation-operation-uid",
+        status: 500,
+        code: "AUDIT_APPEND_FAILED",
+        errorName: "Error",
+        message: "Successful operation audit event could not be appended",
+      },
+    ]);
+    expect(JSON.stringify(logs)).not.toContain("audit unavailable");
+    expect(JSON.stringify(logs)).not.toContain("private-request");
+    expect(JSON.stringify(logs)).not.toContain("do-not-store");
     expect(
       await operationStore.get("operation-operation-uid"),
     ).not.toHaveProperty("spec.request");