diff --git a/app/attachment_channel.ts b/app/attachment_channel.ts
index 01cccd1bdb..f8243cde28 100644
--- a/app/attachment_channel.ts
+++ b/app/attachment_channel.ts
@@ -443,12 +443,15 @@ function deleteOrphanedAttachments({
         await sql.sqlRead('finishGetKnownMessageAttachments', cursor);
       }
     }
-
     log.info(
-      `cleanupOrphanedAttachments:  ${totalAttachmentsFound} message ` +
-        `attachments; ${orphanedAttachments.size} remain`
+      `cleanupOrphanedAttachments: ${totalAttachmentsFound} attachments and \
+      ${totalDownloadsFound} downloads found on disk`
     );
 
+    if (orphanedAttachments.size > 0) {
+      log.error(`${orphanedAttachments.size} orphaned attachment(s) found`);
+    }
+
     if (totalMissing > 0) {
       log.warn(
         `cleanupOrphanedAttachments: ${totalMissing} message attachments were not found on disk`
@@ -460,10 +463,10 @@ function deleteOrphanedAttachments({
       attachments: Array.from(orphanedAttachments),
     });
 
-    log.info(
-      `cleanupOrphanedAttachments: found ${totalDownloadsFound} downloads ` +
-        `${orphanedDownloads.size} remain`
-    );
+    if (orphanedDownloads.size > 0) {
+      log.error(`${orphanedDownloads.size} orphaned download(s) found`);
+    }
+
     await deleteAllDownloads({
       userDataPath,
       downloads: Array.from(orphanedDownloads),
diff --git a/ts/RemoteConfig.ts b/ts/RemoteConfig.ts
index 5adaec1f27..fef90df2a1 100644
--- a/ts/RemoteConfig.ts
+++ b/ts/RemoteConfig.ts
@@ -28,6 +28,7 @@ const KnownConfigKeys = [
   'desktop.donations',
   'desktop.donations.prod',
   'desktop.internalUser',
+  'desktop.loggingErrorToasts',
   'desktop.mediaQuality.levels',
   'desktop.messageCleanup',
   'desktop.retryRespondMaxAge',
diff --git a/ts/components/ToastManager.stories.tsx b/ts/components/ToastManager.stories.tsx
index 5041ec651a..9b669c0d47 100644
--- a/ts/components/ToastManager.stories.tsx
+++ b/ts/components/ToastManager.stories.tsx
@@ -152,6 +152,11 @@ function getToast(toastType: ToastType): AnyToast {
       return { toastType: ToastType.LinkCopied };
     case ToastType.LoadingFullLogs:
       return { toastType: ToastType.LoadingFullLogs };
+    case ToastType._InternalMainProcessLoggingError:
+      return {
+        toastType: ToastType._InternalMainProcessLoggingError,
+        parameters: { logLines: ['error1', 'error2'], count: 2 },
+      };
     case ToastType.MaxAttachments:
       return { toastType: ToastType.MaxAttachments };
     case ToastType.MediaNoLongerAvailable:
diff --git a/ts/components/ToastManager.tsx b/ts/components/ToastManager.tsx
index 95bda157a7..d93854c1b4 100644
--- a/ts/components/ToastManager.tsx
+++ b/ts/components/ToastManager.tsx
@@ -19,6 +19,7 @@ import type { LocalizerType } from '../types/Util.js';
 import type { AnyToast } from '../types/Toast.js';
 import type { AnyActionableMegaphone } from '../types/Megaphone.js';
 import type { Location } from '../types/Nav.js';
+import { tw } from '../axo/tw.js';
 
 export type PropsType = {
   changeLocation: (newLocation: Location) => unknown;
@@ -586,6 +587,40 @@ export function renderToast({
     );
   }
 
+  if (toastType === ToastType._InternalMainProcessLoggingError) {
+    return (
+      <Toast
+        autoDismissDisabled
+        onClose={hideToast}
+        toastAction={{
+          label: i18n('icu:Toast__ActionLabel--SubmitLog'),
+          onClick: onShowDebugLog,
+        }}
+        // eslint-disable-next-line better-tailwindcss/no-restricted-classes
+        className={tw('max-w-[640px]!')}
+      >
+        <h2>
+          [INTERNAL]: {toast.parameters.count} error(s) from main process,
+          please submit log.
+        </h2>
+
+        {toast.parameters.count > toast.parameters.logLines.length ? (
+          <h3
+            className={tw('my-2')}
+          >{`Showing only last ${toast.parameters.logLines.length} errors`}</h3>
+        ) : null}
+
+        <pre
+          className={tw(
+            'my-2 max-h-48 min-h-24 max-w-[520px] overflow-auto border-1 border-solid p-2'
+          )}
+        >
+          {toast.parameters.logLines.join('\n')}
+        </pre>
+      </Toast>
+    );
+  }
+
   if (toastType === ToastType.PinnedConversationsFull) {
     return (
       <Toast onClose={hideToast}>{i18n('icu:pinnedConversationsFull')}</Toast>
diff --git a/ts/logging/log.ts b/ts/logging/log.ts
index a55712e5db..9e9a880194 100644
--- a/ts/logging/log.ts
+++ b/ts/logging/log.ts
@@ -38,6 +38,13 @@ const SUBSYSTEM_COLORS = new LRUCache<string, string>({
   max: 500,
 });
 
+let onLogCallback: (level: number, logLine: string, msgPrefix?: string) => void;
+export function setOnLogCallback(
+  cb: (level: number, logLine: string, msgPrefix?: string) => void
+): void {
+  onLogCallback = cb;
+}
+
 // Only for unpackaged app
 function getSubsystemColor(name: string): string {
   const cached = SUBSYSTEM_COLORS.get(name);
@@ -168,6 +175,8 @@ const pinoInstance = pino(
             typeof item === 'string' ? item : reallyJsonStringify(item)
           )
           .join(' ');
+        onLogCallback?.(level, line, this.msgPrefix);
+
         return method.call(this, line);
       },
     },
diff --git a/ts/logging/main_process_logging.ts b/ts/logging/main_process_logging.ts
index f6d112e338..5c7df6a1d3 100644
--- a/ts/logging/main_process_logging.ts
+++ b/ts/logging/main_process_logging.ts
@@ -27,10 +27,11 @@ import * as Errors from '../types/errors.js';
 import { createRotatingPinoDest } from '../util/rotatingPinoDest.js';
 import { redactAll } from '../util/privacy.js';
 
-import { setPinoDestination, log } from './log.js';
+import { setPinoDestination, log, setOnLogCallback } from './log.js';
 
 import type { FetchLogIpcData, LogEntryType } from './shared.js';
 import { LogLevel, isLogEntry } from './shared.js';
+import { isProduction } from '../util/version.js';
 
 const { filter, flatten, map, pick, sortBy } = lodash;
 
@@ -47,6 +48,17 @@ export async function initialize(
   }
   isInitialized = true;
 
+  if (!isProduction(app.getVersion())) {
+    setOnLogCallback((level, logLine, msgPrefix) => {
+      if (level >= LogLevel.Error) {
+        getMainWindow()?.webContents.send(
+          'logging-error',
+          `${msgPrefix ? `${msgPrefix}` : ''}${logLine}`
+        );
+      }
+    });
+  }
+
   const basePath = app.getPath('userData');
   const logPath = join(basePath, 'logs');
   mkdirSync(logPath, { recursive: true });
diff --git a/ts/types/Toast.tsx b/ts/types/Toast.tsx
index e1de4c0a37..e2cf6aeeb8 100644
--- a/ts/types/Toast.tsx
+++ b/ts/types/Toast.tsx
@@ -54,6 +54,7 @@ export enum ToastType {
   LeftGroup = 'LeftGroup',
   LinkCopied = 'LinkCopied',
   LoadingFullLogs = 'LoadingFullLogs',
+  _InternalMainProcessLoggingError = '_InternalMainProcessLoggingError',
   MaxAttachments = 'MaxAttachments',
   MediaNoLongerAvailable = 'MediaNoLongerAvailable',
   MessageBodyTooLong = 'MessageBodyTooLong',
@@ -165,6 +166,10 @@ export type AnyToast =
   | { toastType: ToastType.LeftGroup }
   | { toastType: ToastType.LinkCopied }
   | { toastType: ToastType.LoadingFullLogs }
+  | {
+      toastType: ToastType._InternalMainProcessLoggingError;
+      parameters: { count: number; logLines: Array<string> };
+    }
   | { toastType: ToastType.MaxAttachments }
   | { toastType: ToastType.MediaNoLongerAvailable }
   | { toastType: ToastType.MessageBodyTooLong }
diff --git a/ts/windows/main/phase1-ipc.ts b/ts/windows/main/phase1-ipc.ts
index 07d1f63606..375ce91775 100644
--- a/ts/windows/main/phase1-ipc.ts
+++ b/ts/windows/main/phase1-ipc.ts
@@ -4,7 +4,7 @@
 import EventEmitter from 'node:events';
 import { ipcRenderer as ipc } from 'electron';
 import * as semver from 'semver';
-import lodash from 'lodash';
+import lodash, { throttle } from 'lodash';
 import PQueue from 'p-queue';
 
 import type { IPCType } from '../../window.d.ts';
@@ -35,6 +35,7 @@ import {
   conversationJobQueue,
   conversationQueueJobEnum,
 } from '../../jobs/conversationJobQueue.js';
+import { isEnabled } from '../../RemoteConfig.js';
 
 const { groupBy, mapValues } = lodash;
 
@@ -499,6 +500,56 @@ ipc.on('sql-error', () => {
   });
 });
 
+let untoastedMainProcessErrorLogCount = 0;
+let untoastedMainProcessErrorLogs: Array<string> = [];
+const MAX_MAIN_PROCESS_ERROR_LOGS_TO_CACHE = 5;
+
+ipc.on('logging-error', (_event, logLine) => {
+  if (isProduction(window.getVersion())) {
+    return;
+  }
+
+  if (!isEnabled('desktop.loggingErrorToasts')) {
+    return;
+  }
+
+  untoastedMainProcessErrorLogCount += 1;
+  const numCached = untoastedMainProcessErrorLogs.unshift(logLine);
+  if (numCached > MAX_MAIN_PROCESS_ERROR_LOGS_TO_CACHE) {
+    untoastedMainProcessErrorLogs.pop();
+  }
+
+  throttledHandleMainProcessErrors();
+});
+
+const throttledHandleMainProcessErrors = throttle(
+  _handleMainProcessErrors,
+  5000
+);
+
+function _handleMainProcessErrors() {
+  if (!window.reduxActions) {
+    // Try again in a bit!
+    throttledHandleMainProcessErrors();
+    return;
+  }
+
+  if (untoastedMainProcessErrorLogs.length === 0) {
+    return;
+  }
+
+  window.reduxActions.toast.showToast({
+    toastType: ToastType._InternalMainProcessLoggingError,
+    parameters: {
+      count: untoastedMainProcessErrorLogCount,
+      logLines: untoastedMainProcessErrorLogs,
+    },
+  });
+
+  untoastedMainProcessErrorLogCount = 0;
+  untoastedMainProcessErrorLogs = [];
+}
+
 ipc.on(
   'art-creator:uploadStickerPack',
   async (