diff --git a/_locales/en/messages.json b/_locales/en/messages.json
index 8b649412b..f9168cc88 100644
--- a/_locales/en/messages.json
+++ b/_locales/en/messages.json
@@ -73,6 +73,7 @@
   "attemptingReconnection": "Attempting reconnect in $reconnect_duration_in_seconds$ seconds",
   "submitDebugLog": "Debug log",
   "debugLog": "Debug Log",
+  "showDebugLog": "Show Debug Log",
   "goToReleaseNotes": "Go to Release Notes",
   "goToSupportPage": "Go to Support Page",
   "menuReportIssue": "Report an Issue",
diff --git a/debug_log_preload.js b/debug_log_preload.js
index 8121af5d6..dbd23deff 100644
--- a/debug_log_preload.js
+++ b/debug_log_preload.js
@@ -22,5 +22,9 @@ window.getNodeVersion = () => config.node_version;
 window.getEnvironment = () => config.environment;
 
 require('./js/logging');
+const os = require('os');
+
+window.getOSRelease = () => `${os.type()} ${os.release} ${os.platform()}`;
+window.getCommitHash = () => config.commitHash;
 
 window.closeDebugLog = () => ipcRenderer.send('close-debug-log');
diff --git a/js/views/debug_log_view.js b/js/views/debug_log_view.js
index 1ed681538..4ef324362 100644
--- a/js/views/debug_log_view.js
+++ b/js/views/debug_log_view.js
@@ -26,9 +26,15 @@
       this.render();
       this.$('textarea').val(i18n('loading'));
 
+      const operatingSystemInfo = `Operating System: ${window.getOSRelease()}`;
+
+      const commitHashInfo = window.getCommitHash() ? `Commit Hash: ${window.getCommitHash()}` : '';
+
       // eslint-disable-next-line more/no-then
       window.log.fetch().then(text => {
-        this.$('textarea').val(text);
+        const debugLogWithSystemInfo = operatingSystemInfo + commitHashInfo + text;
+
+        this.$('textarea').val(debugLogWithSystemInfo);
       });
     },
     events: {
diff --git a/ts/components/conversation/message/OutgoingMessageStatus.tsx b/ts/components/conversation/message/OutgoingMessageStatus.tsx
index 2a6869b75..0701ce131 100644
--- a/ts/components/conversation/message/OutgoingMessageStatus.tsx
+++ b/ts/components/conversation/message/OutgoingMessageStatus.tsx
@@ -1,3 +1,4 @@
+import { ipcRenderer } from 'electron';
 import React from 'react';
 import styled from 'styled-components';
 import { MessageDeliveryStatus } from '../../../models/messageType';
@@ -40,8 +41,12 @@ const MessageStatusRead = () => {
 };
 
 const MessageStatusError = () => {
+  const showDebugLog = () => {
+    ipcRenderer.send('show-debug-log');
+  };
+
   return (
-    <MessageStatusSendingContainer title={window.i18n('sendFailed')}>
+    <MessageStatusSendingContainer onClick={showDebugLog} title={window.i18n('sendFailed')}>
       <SessionIcon iconColor={'var(--color-destructive'} iconType="error" iconSize={'tiny'} />
     </MessageStatusSendingContainer>
   );
diff --git a/ts/components/session/settings/SessionSettings.tsx b/ts/components/session/settings/SessionSettings.tsx
index 05db39c86..487bc236b 100644
--- a/ts/components/session/settings/SessionSettings.tsx
+++ b/ts/components/session/settings/SessionSettings.tsx
@@ -14,7 +14,7 @@ import {
   getPasswordHash,
   hasLinkPreviewPopupBeenDisplayed,
 } from '../../../../ts/data/data';
-import { shell } from 'electron';
+import { ipcRenderer, shell } from 'electron';
 import { mapDispatchToProps } from '../../../state/actions';
 import { unblockConvoById } from '../../../interactions/conversationInteractions';
 import { toggleAudioAutoplay } from '../../../state/ducks/userConfig';
@@ -497,6 +497,23 @@ class SettingsViewInner extends React.Component<SettingsViewProps, State> {
           buttonColor: SessionButtonColor.Primary,
         },
       },
+      {
+        id: 'debug-log-setting',
+        title: window.i18n('showDebugLog'),
+        description: undefined,
+        hidden: false,
+        type: SessionSettingType.Button,
+        category: SessionSettingCategory.Appearance,
+        setFn: undefined,
+        comparisonValue: undefined,
+        onClick: () => {
+          ipcRenderer.send('show-debug-log');
+        },
+        content: {
+          buttonText: window.i18n('debugLog'),
+          buttonColor: SessionButtonColor.Primary,
+        },
+      },
       {
         id: 'media-permissions',
         title: window.i18n('mediaPermissionsTitle'),