diff --git a/packages/replay/src/eventBuffer/EventBufferArray.ts b/packages/replay/src/eventBuffer/EventBufferArray.ts
index c9915e7c8b05..2eb760409d9f 100644
--- a/packages/replay/src/eventBuffer/EventBufferArray.ts
+++ b/packages/replay/src/eventBuffer/EventBufferArray.ts
@@ -10,11 +10,16 @@ import { EventBufferSizeExceededError } from './error';
 export class EventBufferArray implements EventBuffer {
   /** All the events that are buffered to be sent. */
   public events: RecordingEvent[];
+
+  /** @inheritdoc */
+  public hasCheckout: boolean;
+
   private _totalSize: number;
 
   public constructor() {
     this.events = [];
     this._totalSize = 0;
+    this.hasCheckout = false;
   }
 
   /** @inheritdoc */
@@ -59,6 +64,7 @@ export class EventBufferArray implements EventBuffer {
   public clear(): void {
     this.events = [];
     this._totalSize = 0;
+    this.hasCheckout = false;
   }
 
   /** @inheritdoc */
diff --git a/packages/replay/src/eventBuffer/EventBufferCompressionWorker.ts b/packages/replay/src/eventBuffer/EventBufferCompressionWorker.ts
index 8c40c5d289cf..90e1eeba8f11 100644
--- a/packages/replay/src/eventBuffer/EventBufferCompressionWorker.ts
+++ b/packages/replay/src/eventBuffer/EventBufferCompressionWorker.ts
@@ -11,6 +11,9 @@ import { WorkerHandler } from './WorkerHandler';
  * Exported only for testing.
  */
 export class EventBufferCompressionWorker implements EventBuffer {
+  /** @inheritdoc */
+  public hasCheckout: boolean;
+
   private _worker: WorkerHandler;
   private _earliestTimestamp: number | null;
   private _totalSize;
@@ -19,6 +22,7 @@ export class EventBufferCompressionWorker implements EventBuffer {
     this._worker = new WorkerHandler(worker);
     this._earliestTimestamp = null;
     this._totalSize = 0;
+    this.hasCheckout = false;
   }
 
   /** @inheritdoc */
@@ -78,6 +82,8 @@ export class EventBufferCompressionWorker implements EventBuffer {
   public clear(): void {
     this._earliestTimestamp = null;
     this._totalSize = 0;
+    this.hasCheckout = false;
+
     // We do not wait on this, as we assume the order of messages is consistent for the worker
     void this._worker.postMessage('clear');
   }
diff --git a/packages/replay/src/eventBuffer/EventBufferProxy.ts b/packages/replay/src/eventBuffer/EventBufferProxy.ts
index 2b3c2329f876..0b5a6bdfed11 100644
--- a/packages/replay/src/eventBuffer/EventBufferProxy.ts
+++ b/packages/replay/src/eventBuffer/EventBufferProxy.ts
@@ -35,6 +35,15 @@ export class EventBufferProxy implements EventBuffer {
     return this._used.hasEvents;
   }
 
+  /** @inheritdoc */
+  public get hasCheckout(): boolean {
+    return this._used.hasCheckout;
+  }
+  /** @inheritdoc */
+  public set hasCheckout(value: boolean) {
+    this._used.hasCheckout = value;
+  }
+
   /** @inheritDoc */
   public destroy(): void {
     this._fallback.destroy();
diff --git a/packages/replay/src/replay.ts b/packages/replay/src/replay.ts
index c66d1d914d82..dd82e26f3d57 100644
--- a/packages/replay/src/replay.ts
+++ b/packages/replay/src/replay.ts
@@ -47,7 +47,7 @@ import { debounce } from './util/debounce';
 import { getHandleRecordingEmit } from './util/handleRecordingEmit';
 import { isExpired } from './util/isExpired';
 import { isSessionExpired } from './util/isSessionExpired';
-import { logInfo } from './util/log';
+import { logInfo, logInfoNextTick } from './util/log';
 import { sendReplay } from './util/sendReplay';
 import type { SKIPPED } from './util/throttle';
 import { throttle, THROTTLED } from './util/throttle';
@@ -250,7 +250,10 @@ export class ReplayContainer implements ReplayContainerInterface {
       this.recordingMode = 'buffer';
     }
 
-    logInfo(`[Replay] Starting replay in ${this.recordingMode} mode`, this._options._experiments.traceInternals);
+    logInfoNextTick(
+      `[Replay] Starting replay in ${this.recordingMode} mode`,
+      this._options._experiments.traceInternals,
+    );
 
     this._initializeRecording();
   }
@@ -271,7 +274,7 @@ export class ReplayContainer implements ReplayContainerInterface {
       throw new Error('Replay buffering is in progress, call `flush()` to save the replay');
     }
 
-    logInfo('[Replay] Starting replay in session mode', this._options._experiments.traceInternals);
+    logInfoNextTick('[Replay] Starting replay in session mode', this._options._experiments.traceInternals);
 
     const previousSessionId = this.session && this.session.id;
 
@@ -300,7 +303,7 @@ export class ReplayContainer implements ReplayContainerInterface {
       throw new Error('Replay recording is already in progress');
     }
 
-    logInfo('[Replay] Starting replay in buffer mode', this._options._experiments.traceInternals);
+    logInfoNextTick('[Replay] Starting replay in buffer mode', this._options._experiments.traceInternals);
 
     const previousSessionId = this.session && this.session.id;
 
@@ -1151,6 +1154,12 @@ export class ReplayContainer implements ReplayContainerInterface {
       return;
     }
 
+    const eventBuffer = this.eventBuffer;
+    if (eventBuffer && this.session.segmentId === 0 && !eventBuffer.hasCheckout) {
+      logInfo('[Replay] Flushing initial segment without checkout.', this._options._experiments.traceInternals);
+      // TODO FN: Evaluate if we want to stop here, or remove this again?
+    }
+
     // this._flushLock acts as a lock so that future calls to `_flush()`
     // will be blocked until this promise resolves
     if (!this._flushLock) {
diff --git a/packages/replay/src/session/fetchSession.ts b/packages/replay/src/session/fetchSession.ts
index 2d8f3f98a8aa..43e162b5f3d6 100644
--- a/packages/replay/src/session/fetchSession.ts
+++ b/packages/replay/src/session/fetchSession.ts
@@ -1,7 +1,7 @@
 import { REPLAY_SESSION_KEY, WINDOW } from '../constants';
 import type { Session } from '../types';
 import { hasSessionStorage } from '../util/hasSessionStorage';
-import { logInfo } from '../util/log';
+import { logInfoNextTick } from '../util/log';
 import { makeSession } from './Session';
 
 /**
@@ -22,7 +22,7 @@ export function fetchSession(traceInternals?: boolean): Session | null {
 
     const sessionObj = JSON.parse(sessionStringFromStorage) as Session;
 
-    logInfo('[Replay] Loading existing session', traceInternals);
+    logInfoNextTick('[Replay] Loading existing session', traceInternals);
 
     return makeSession(sessionObj);
   } catch {
diff --git a/packages/replay/src/session/getSession.ts b/packages/replay/src/session/getSession.ts
index b26921e58938..da3184f05296 100644
--- a/packages/replay/src/session/getSession.ts
+++ b/packages/replay/src/session/getSession.ts
@@ -1,6 +1,6 @@
 import type { Session, SessionOptions, Timeouts } from '../types';
 import { isSessionExpired } from '../util/isSessionExpired';
-import { logInfo } from '../util/log';
+import { logInfoNextTick } from '../util/log';
 import { createSession } from './createSession';
 import { fetchSession } from './fetchSession';
 import { makeSession } from './Session';
@@ -44,10 +44,10 @@ export function getSession({
       // and when this session is expired, it will not be renewed until user
       // reloads.
       const discardedSession = makeSession({ sampled: false });
-      logInfo('[Replay] Session should not be refreshed', traceInternals);
+      logInfoNextTick('[Replay] Session should not be refreshed', traceInternals);
       return { type: 'new', session: discardedSession };
     } else {
-      logInfo('[Replay] Session has expired', traceInternals);
+      logInfoNextTick('[Replay] Session has expired', traceInternals);
     }
     // Otherwise continue to create a new session
   }
@@ -57,7 +57,7 @@ export function getSession({
     sessionSampleRate,
     allowBuffering,
   });
-  logInfo('[Replay] Created new session', traceInternals);
+  logInfoNextTick('[Replay] Created new session', traceInternals);
 
   return { type: 'new', session: newSession };
 }
diff --git a/packages/replay/src/types/replay.ts b/packages/replay/src/types/replay.ts
index 46f1e8f4ef93..1fbf44aa1b95 100644
--- a/packages/replay/src/types/replay.ts
+++ b/packages/replay/src/types/replay.ts
@@ -389,6 +389,11 @@ export interface EventBuffer {
    */
   readonly type: EventBufferType;
 
+  /**
+   * If the event buffer contains a checkout event.
+   */
+  hasCheckout: boolean;
+
   /**
    * Destroy the event buffer.
    */
diff --git a/packages/replay/src/util/addEvent.ts b/packages/replay/src/util/addEvent.ts
index 4718675700a9..d1e1d366a9e9 100644
--- a/packages/replay/src/util/addEvent.ts
+++ b/packages/replay/src/util/addEvent.ts
@@ -42,6 +42,7 @@ export async function addEvent(
   try {
     if (isCheckout && replay.recordingMode === 'buffer') {
       replay.eventBuffer.clear();
+      replay.eventBuffer.hasCheckout = true;
     }
 
     const replayOptions = replay.getOptions();
diff --git a/packages/replay/src/util/log.ts b/packages/replay/src/util/log.ts
index fbb107ad48f7..9aa650a81264 100644
--- a/packages/replay/src/util/log.ts
+++ b/packages/replay/src/util/log.ts
@@ -11,22 +11,42 @@ export function logInfo(message: string, shouldAddBreadcrumb?: boolean): void {
 
   logger.info(message);
 
+  if (shouldAddBreadcrumb) {
+    addBreadcrumb(message);
+  }
+}
+
+/**
+ * Log a message, and add a breadcrumb in the next tick.
+ * This is necessary when the breadcrumb may be added before the replay is initialized.
+ */
+export function logInfoNextTick(message: string, shouldAddBreadcrumb?: boolean): void {
+  if (!__DEBUG_BUILD__) {
+    return;
+  }
+
+  logger.info(message);
+
   if (shouldAddBreadcrumb) {
     // Wait a tick here to avoid race conditions for some initial logs
     // which may be added before replay is initialized
     setTimeout(() => {
-      const hub = getCurrentHub();
-      hub.addBreadcrumb(
-        {
-          category: 'console',
-          data: {
-            logger: 'replay',
-          },
-          level: 'info',
-          message,
-        },
-        { level: 'info' },
-      );
+      addBreadcrumb(message);
     }, 0);
   }
 }
+
+function addBreadcrumb(message: string): void {
+  const hub = getCurrentHub();
+  hub.addBreadcrumb(
+    {
+      category: 'console',
+      data: {
+        logger: 'replay',
+      },
+      level: 'info',
+      message,
+    },
+    { level: 'info' },
+  );
+}
diff --git a/packages/replay/test/integration/flush.test.ts b/packages/replay/test/integration/flush.test.ts
index a4fbdb464ae4..611a1043df1a 100644
--- a/packages/replay/test/integration/flush.test.ts
+++ b/packages/replay/test/integration/flush.test.ts
@@ -1,6 +1,6 @@
 import * as SentryUtils from '@sentry/utils';
 
-import { DEFAULT_FLUSH_MIN_DELAY, WINDOW } from '../../src/constants';
+import { DEFAULT_FLUSH_MIN_DELAY, MAX_SESSION_LIFE, WINDOW } from '../../src/constants';
 import type { ReplayContainer } from '../../src/replay';
 import { clearSession } from '../../src/session/clearSession';
 import type { EventBuffer } from '../../src/types';
@@ -286,15 +286,22 @@ describe('Integration | flush', () => {
 
     expect(mockFlush).toHaveBeenCalledTimes(20);
     expect(mockSendReplay).toHaveBeenCalledTimes(1);
+
+    replay.getOptions().minReplayDuration = 0;
   });
 
   it('does not flush if session is too long', async () => {
     replay.timeouts.maxSessionLife = 100_000;
-    jest.setSystemTime(new Date(BASE_TIMESTAMP));
+    jest.setSystemTime(BASE_TIMESTAMP);
 
     sessionStorage.clear();
     clearSession(replay);
     replay['_loadAndCheckSession']();
+    // No-op _loadAndCheckSession to avoid us resetting the session for this test
+    const _tmp = replay['_loadAndCheckSession'];
+    replay['_loadAndCheckSession'] = () => {
+      return true;
+    };
 
     await advanceTimers(120_000);
 
@@ -308,7 +315,71 @@ describe('Integration | flush', () => {
     mockRecord._emitter(TEST_EVENT);
 
     await advanceTimers(DEFAULT_FLUSH_MIN_DELAY);
+
     expect(mockFlush).toHaveBeenCalledTimes(1);
     expect(mockSendReplay).toHaveBeenCalledTimes(0);
+
+    replay.timeouts.maxSessionLife = MAX_SESSION_LIFE;
+    replay['_loadAndCheckSession'] = _tmp;
+  });
+
+  it('logs warning if flushing initial segment without checkout', async () => {
+    replay.getOptions()._experiments.traceInternals = true;
+
+    sessionStorage.clear();
+    clearSession(replay);
+    replay['_loadAndCheckSession']();
+    await new Promise(process.nextTick);
+    jest.setSystemTime(BASE_TIMESTAMP);
+
+    // Clear the event buffer to simulate no checkout happened
+    replay.eventBuffer!.clear();
+
+    // click happens first
+    domHandler({
+      name: 'click',
+    });
+
+    // no checkout!
+    await advanceTimers(DEFAULT_FLUSH_MIN_DELAY);
+
+    expect(mockFlush).toHaveBeenCalledTimes(1);
+    expect(mockSendReplay).toHaveBeenCalledTimes(1);
+
+    const replayData = mockSendReplay.mock.calls[0][0];
+
+    expect(JSON.parse(replayData.recordingData)).toEqual([
+      {
+        type: 5,
+        timestamp: BASE_TIMESTAMP,
+        data: {
+          tag: 'breadcrumb',
+          payload: {
+            timestamp: BASE_TIMESTAMP / 1000,
+            type: 'default',
+            category: 'ui.click',
+            message: '<unknown>',
+            data: {},
+          },
+        },
+      },
+      {
+        type: 5,
+        timestamp: BASE_TIMESTAMP + DEFAULT_FLUSH_MIN_DELAY,
+        data: {
+          tag: 'breadcrumb',
+          payload: {
+            timestamp: (BASE_TIMESTAMP + DEFAULT_FLUSH_MIN_DELAY) / 1000,
+            type: 'default',
+            category: 'console',
+            data: { logger: 'replay' },
+            level: 'info',
+            message: '[Replay] Flushing initial segment without checkout.',
+          },
+        },
+      },
+    ]);
+
+    replay.getOptions()._experiments.traceInternals = false;
   });
 });