diff --git a/components/server/src/jobs/runner.ts b/components/server/src/jobs/runner.ts
index dfcc27ed5afedd..b601da6db7141c 100644
--- a/components/server/src/jobs/runner.ts
+++ b/components/server/src/jobs/runner.ts
@@ -18,6 +18,7 @@ import { WebhookEventGarbageCollector } from "./webhook-gc";
 import { WorkspaceGarbageCollector } from "./workspace-gc";
 import { SnapshotsJob } from "./snapshots";
 import { RelationshipUpdateJob } from "../authorization/relationship-updater-job";
+import { runWithContext } from "../util/log-context";
 
 export const Job = Symbol("Job");
 
@@ -78,29 +79,31 @@ export class JobRunner {
 
         try {
             await this.mutex.using([job.name, ...(job.lockedResources || [])], job.frequencyMs, async (signal) => {
-                log.info(`Acquired lock for job ${job.name}.`, logCtx);
-                // we want to hold the lock for the entire duration of the job, so we return earliest after frequencyMs
-                const timeout = new Promise<void>((resolve) => setTimeout(resolve, job.frequencyMs));
-                const timer = jobsDurationSeconds.startTimer({ name: job.name });
-                reportJobStarted(job.name);
-                const now = new Date().getTime();
-                try {
-                    await job.run();
-                    log.info(`Successfully finished job ${job.name}`, {
-                        ...logCtx,
-                        jobTookSec: `${(new Date().getTime() - now) / 1000}s`,
-                    });
-                    reportJobCompleted(job.name, true);
-                } catch (err) {
-                    log.error(`Error while running job ${job.name}`, err, {
-                        ...logCtx,
-                        jobTookSec: `${(new Date().getTime() - now) / 1000}s`,
-                    });
-                    reportJobCompleted(job.name, false);
-                } finally {
-                    jobsDurationSeconds.observe(timer());
-                    await timeout;
-                }
+                await runWithContext(job.name, {}, async () => {
+                    log.info(`Acquired lock for job ${job.name}.`, logCtx);
+                    // we want to hold the lock for the entire duration of the job, so we return earliest after frequencyMs
+                    const timeout = new Promise<void>((resolve) => setTimeout(resolve, job.frequencyMs));
+                    const timer = jobsDurationSeconds.startTimer({ name: job.name });
+                    reportJobStarted(job.name);
+                    const now = new Date().getTime();
+                    try {
+                        await job.run();
+                        log.info(`Successfully finished job ${job.name}`, {
+                            ...logCtx,
+                            jobTookSec: `${(new Date().getTime() - now) / 1000}s`,
+                        });
+                        reportJobCompleted(job.name, true);
+                    } catch (err) {
+                        log.error(`Error while running job ${job.name}`, err, {
+                            ...logCtx,
+                            jobTookSec: `${(new Date().getTime() - now) / 1000}s`,
+                        });
+                        reportJobCompleted(job.name, false);
+                    } finally {
+                        jobsDurationSeconds.observe(timer());
+                        await timeout;
+                    }
+                });
             });
         } catch (err) {
             if (err instanceof ResourceLockedError || err instanceof ExecutionError) {
diff --git a/components/server/src/messaging/redis-subscriber.ts b/components/server/src/messaging/redis-subscriber.ts
index 5f56104180338d..3becb5fbaa4a47 100644
--- a/components/server/src/messaging/redis-subscriber.ts
+++ b/components/server/src/messaging/redis-subscriber.ts
@@ -29,6 +29,7 @@ import {
 } from "../prometheus-metrics";
 import { Redis } from "ioredis";
 import { WorkspaceDB } from "@gitpod/gitpod-db/lib";
+import { runWithContext } from "../util/log-context";
 
 const UNDEFINED_KEY = "undefined";
 
@@ -54,18 +55,20 @@ export class RedisSubscriber {
         }
 
         this.redis.on("message", async (channel: string, message: string) => {
-            reportRedisUpdateReceived(channel);
-
-            let err: Error | undefined;
-            try {
-                await this.onMessage(channel, message);
-                log.debug("[redis] Succesfully handled update", { channel, message });
-            } catch (e) {
-                err = e;
-                log.error("[redis] Failed to handle message from Pub/Sub", e, { channel, message });
-            } finally {
-                reportRedisUpdateCompleted(channel, err);
-            }
+            await runWithContext("redis-subscriber", {}, async () => {
+                reportRedisUpdateReceived(channel);
+
+                let err: Error | undefined;
+                try {
+                    await this.onMessage(channel, message);
+                    log.debug("[redis] Succesfully handled update", { channel, message });
+                } catch (e) {
+                    err = e;
+                    log.error("[redis] Failed to handle message from Pub/Sub", e, { channel, message });
+                } finally {
+                    reportRedisUpdateCompleted(channel, err);
+                }
+            });
         });
     }
 
diff --git a/components/server/src/server.ts b/components/server/src/server.ts
index 8449844fcfe5df..7bfeb58c5b9548 100644
--- a/components/server/src/server.ts
+++ b/components/server/src/server.ts
@@ -47,6 +47,7 @@ import { GitHubEnterpriseApp } from "./prebuilds/github-enterprise-app";
 import { JobRunner } from "./jobs/runner";
 import { RedisSubscriber } from "./messaging/redis-subscriber";
 import { HEADLESS_LOGS_PATH_PREFIX, HEADLESS_LOG_DOWNLOAD_PATH_PREFIX } from "./workspace/headless-log-service";
+import { runWithContext } from "./util/log-context";
 
 @injectable()
 export class Server {
@@ -138,6 +139,16 @@ export class Server {
         // Install passport
         await this.authenticator.init(app);
 
+        // log context
+        app.use(async (req: express.Request, res: express.Response, next: express.NextFunction) => {
+            try {
+                const userId = req.user ? req.user.id : undefined;
+                await runWithContext("http", { userId }, () => next());
+            } catch (err) {
+                next(err);
+            }
+        });
+
         // Ensure that host contexts of dynamic auth providers are initialized.
         await this.hostCtxProvider.init();
 
diff --git a/components/server/src/util/log-context.ts b/components/server/src/util/log-context.ts
index 8d76ea93071c21..400efcf1f84dea 100644
--- a/components/server/src/util/log-context.ts
+++ b/components/server/src/util/log-context.ts
@@ -13,24 +13,33 @@ import { v4 } from "uuid";
 type EnhancedLogContext = LogContext & {
     contextId?: string;
     contextTimeMs: number;
+    contextKind: string;
 };
+
 const asyncLocalStorage = new AsyncLocalStorage<EnhancedLogContext>();
 const augmenter: LogContext.Augmenter = (ctx) => {
     const globalContext = asyncLocalStorage.getStore();
-    const contextTime = globalContext?.contextTimeMs ? Date.now() - globalContext.contextTimeMs : undefined;
-    return {
+    const contextTimeMs = globalContext?.contextTimeMs ? Date.now() - globalContext.contextTimeMs : undefined;
+    const result = {
         ...globalContext,
-        contextTime,
+        contextTimeMs,
         ...ctx,
     };
+    // if its an empty object return undefined
+    return Object.keys(result).length === 0 ? undefined : result;
 };
 LogContext.setAugmenter(augmenter);
 
-export async function runWithContext<T>(context: LogContext, fun: () => T): Promise<T> {
+export async function runWithContext<T>(
+    contextKind: string,
+    context: LogContext & { contextId?: string },
+    fun: () => T,
+): Promise<T> {
     return asyncLocalStorage.run(
         {
             ...context,
-            contextId: v4(),
+            contextKind,
+            contextId: context.contextId || v4(),
             contextTimeMs: Date.now(),
         },
         fun,
diff --git a/components/server/src/websocket/websocket-connection-manager.ts b/components/server/src/websocket/websocket-connection-manager.ts
index 6eeea6e96c41ee..946fee7e328a7b 100644
--- a/components/server/src/websocket/websocket-connection-manager.ts
+++ b/components/server/src/websocket/websocket-connection-manager.ts
@@ -374,21 +374,33 @@ class GitpodJsonRpcProxyFactory<T extends object> extends JsonRpcProxyFactory<T>
     }
 
     protected async onRequest(method: string, ...args: any[]): Promise<any> {
+        const span = TraceContext.startSpan(method, undefined);
         const userId = this.clientMetadata.userId;
+        const requestId = span.context().toTraceId();
         return runWithContext(
+            "request",
             {
                 userId,
+                contextId: requestId,
             },
             () => {
-                return this.internalOnRequest(method, ...args);
+                try {
+                    return this.internalOnRequest(span, requestId, method, ...args);
+                } finally {
+                    span.finish();
+                }
             },
         );
     }
 
-    private async internalOnRequest(method: string, ...args: any[]): Promise<any> {
-        const span = TraceContext.startSpan(method, undefined);
-        const ctx = { span };
+    private async internalOnRequest(
+        span: opentracing.Span,
+        requestId: string,
+        method: string,
+        ...args: any[]
+    ): Promise<any> {
         const userId = this.clientMetadata.userId;
+        const ctx = { span };
         const timer = apiCallDurationHistogram.startTimer();
         try {
             // generic tracing data
@@ -432,7 +444,7 @@ class GitpodJsonRpcProxyFactory<T extends object> extends JsonRpcProxyFactory<T>
             observeAPICallsDuration(method, 200, timer());
             return result;
         } catch (e) {
-            const traceID = span.context().toTraceId();
+            const requestIdMessage = ` If this error is unexpected, please quote the request ID '${requestId}' when reaching out to Gitpod Support.`;
             if (ApplicationError.hasErrorCode(e)) {
                 increaseApiCallCounter(method, e.code);
                 observeAPICallsDuration(method, e.code, timer());
@@ -449,13 +461,13 @@ class GitpodJsonRpcProxyFactory<T extends object> extends JsonRpcProxyFactory<T>
                         message: e.message,
                     },
                 );
-                throw new ResponseError(e.code, e.message, e.data);
+                throw new ResponseError(e.code, e.message + requestIdMessage, e.data);
             } else {
                 TraceContext.setError(ctx, e); // this is a "real" error
 
                 const err = new ApplicationError(
                     ErrorCodes.INTERNAL_SERVER_ERROR,
-                    `Internal server error. Please quote trace ID: '${traceID}' when reaching to Gitpod Support`,
+                    `Internal server error: '${e.message}'` + requestIdMessage,
                 );
                 increaseApiCallCounter(method, err.code);
                 observeAPICallsDuration(method, err.code, timer());
@@ -464,8 +476,6 @@ class GitpodJsonRpcProxyFactory<T extends object> extends JsonRpcProxyFactory<T>
                 log.error({ userId }, `Request ${method} failed with internal server error`, e, { method, args });
                 throw new ResponseError(ErrorCodes.INTERNAL_SERVER_ERROR, e.message);
             }
-        } finally {
-            span.finish();
         }
     }
 
diff --git a/components/server/src/workspace/workspace-starter.ts b/components/server/src/workspace/workspace-starter.ts
index c9f746497be0a8..5541a93f65ba3a 100644
--- a/components/server/src/workspace/workspace-starter.ts
+++ b/components/server/src/workspace/workspace-starter.ts
@@ -484,9 +484,13 @@ export class WorkspaceStarter {
         const span = TraceContext.startSpan("actuallyStartWorkspace", ctx);
         const region = instance.configuration.regionPreference;
         span.setTag("region_preference", region);
-        log.info("Attempting to start workspace", {
-            instanceID: instance.id,
-            userID: user.id,
+        const logCtx: LogContext = {
+            instanceId: instance.id,
+            userId: user.id,
+            organizationId: workspace.organizationId,
+            workspaceId: workspace.id,
+        };
+        log.info(logCtx, "Attempting to start workspace", {
             forceRebuild: forceRebuild,
         });
 
@@ -524,18 +528,10 @@ export class WorkspaceStarter {
             const ideUrlPromise = new Deferred<string>();
             const before = Date.now();
             const logSuccess = (fromWsManager: boolean) => {
-                log.info(
-                    {
-                        instanceId: instance.id,
-                        userId: workspace.ownerId,
-                        workspaceId: workspace.id,
-                    },
-                    "Received ideURL",
-                    {
-                        tookMs: Date.now() - before,
-                        fromWsManager,
-                    },
-                );
+                log.info(logCtx, "Received ideURL", {
+                    tookMs: Date.now() - before,
+                    fromWsManager,
+                });
             };
 
             const doStartWorkspace = async () => {
@@ -623,7 +619,7 @@ export class WorkspaceStarter {
                 intervalHandle.dispose();
             }
         } catch (err) {
-            this.logAndTraceStartWorkspaceError({ span }, { userId: user.id, instanceId: instance.id }, err);
+            this.logAndTraceStartWorkspaceError({ span }, logCtx, err);
 
             return { instanceID: instance.id };
         } finally {