diff --git a/.yarn/cache/@electron-remote-npm-2.0.10-3aed80e4c3-74ab6fca79.zip b/.yarn/cache/@electron-remote-npm-2.0.12-5e52b64e18-63b5c729bb.zip
similarity index 72%
rename from .yarn/cache/@electron-remote-npm-2.0.10-3aed80e4c3-74ab6fca79.zip
rename to .yarn/cache/@electron-remote-npm-2.0.12-5e52b64e18-63b5c729bb.zip
index dd88f72c5..ae77cd0e9 100644
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diff --git a/.yarn/cache/@types-node-npm-16.18.39-3927a64c2e-eac9b202b7.zip b/.yarn/cache/@types-node-npm-16.18.39-3927a64c2e-eac9b202b7.zip
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diff --git a/.yarn/cache/compare-versions-npm-6.1.0-43f6eabab2-d4e2a45706.zip b/.yarn/cache/compare-versions-npm-6.1.0-43f6eabab2-d4e2a45706.zip
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diff --git a/.yarn/cache/electron-npm-22.3.24-fac8e85d2a-28f0134e7e.zip b/.yarn/cache/electron-npm-22.3.24-fac8e85d2a-28f0134e7e.zip
deleted file mode 100644
index 8f0e8f97f..000000000
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diff --git a/.yarn/cache/electron-npm-27.0.0-210e9ddea3-4a84cb894d.zip b/.yarn/cache/electron-npm-27.0.0-210e9ddea3-4a84cb894d.zip
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deleted file mode 100644
index 900b736a8..000000000
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diff --git a/.yarn/cache/electron-updater-npm-6.1.5-9d5ee245d1-07d6cf1d3d.zip b/.yarn/cache/electron-updater-npm-6.1.5-9d5ee245d1-07d6cf1d3d.zip
new file mode 100644
index 000000000..11ad363c0
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diff --git a/.yarn/cache/mobx-npm-6.10.2-946dc29b68-14d6f1db4e.zip b/.yarn/cache/mobx-npm-6.10.2-946dc29b68-14d6f1db4e.zip
new file mode 100644
index 000000000..8577082bb
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diff --git a/.yarn/cache/tiny-typed-emitter-npm-2.1.0-11a189c3ee-709bca4100.zip b/.yarn/cache/tiny-typed-emitter-npm-2.1.0-11a189c3ee-709bca4100.zip
new file mode 100644
index 000000000..fb6df1882
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diff --git a/.yarn/cache/typed-emitter-npm-2.1.0-0c02187bf2-95821a9e05.zip b/.yarn/cache/typed-emitter-npm-2.1.0-0c02187bf2-95821a9e05.zip
deleted file mode 100644
index 33dfe805c..000000000
Binary files a/.yarn/cache/typed-emitter-npm-2.1.0-0c02187bf2-95821a9e05.zip and /dev/null differ
diff --git a/packages/desktop/app/application.ts b/packages/desktop/app/application.ts
index c268cd537..f83f9378f 100644
--- a/packages/desktop/app/application.ts
+++ b/packages/desktop/app/application.ts
@@ -1,4 +1,4 @@
-import { App, Shell } from 'electron'
+import { App, Shell, Event } from 'electron'
 import { AppState } from './AppState'
 import { createExtensionsServer } from './javascripts/Main/ExtensionsServer'
 import { Keychain } from './javascripts/Main/Keychain/Keychain'
@@ -52,7 +52,7 @@ function focusWindow(appState: AppState) {
 }
 
 function registerSingleInstanceHandler(app: Electron.App, appState: AppState) {
-  app.on('second-instance', (_event: Event, argv: string[]) => {
+  app.on('second-instance', (_event: Event, argv: string[], _workingDirectory: string, _additionalData: unknown) => {
     if (isWindows()) {
       appState.deepLinkUrl = argv.find((arg) => arg.startsWith(deepLinkScheme))
     }
diff --git a/packages/desktop/app/javascripts/Main/UpdateManager.ts b/packages/desktop/app/javascripts/Main/UpdateManager.ts
index 8aae005d0..3dc4a6b82 100644
--- a/packages/desktop/app/javascripts/Main/UpdateManager.ts
+++ b/packages/desktop/app/javascripts/Main/UpdateManager.ts
@@ -174,7 +174,7 @@ export async function checkForUpdate(appState: AppState, state: UpdateState, use
     state.setCheckingForUpdate(true)
 
     try {
-      const result = await autoUpdater.checkForUpdates()
+      const result = userTriggered ? await autoUpdater.checkForUpdatesAndNotify() : await autoUpdater.checkForUpdates()
 
       if (!result) {
         return
diff --git a/packages/desktop/app/stylesheets/renderer.css b/packages/desktop/app/stylesheets/renderer.css
index 02eba8bcd..37daac5f8 100644
--- a/packages/desktop/app/stylesheets/renderer.css
+++ b/packages/desktop/app/stylesheets/renderer.css
@@ -69,12 +69,44 @@ panel-resizer {
   font-size: 0;
 }
 
-/* Required for BrowserWindow titleBarStyle: 'hiddenInset' */
-.mac-desktop #navigation,
-.mac-desktop #navigation .section-title-bar,
-.mac-desktop #items-title-bar,
-.mac-desktop #editor-title-bar,
-.mac-desktop #lock-screen {
+/* https://github.com/electron/electron/issues/37789 */
+.mac-desktop #navigation {
+  -webkit-app-region: drag;
+}
+
+.mac-desktop #navigation-content {
+  -webkit-app-region: no-drag;
+}
+
+.mac-desktop #navigation-content .section-title-bar .title {
+  -webkit-app-region: drag;
+}
+
+.mac-desktop #items-title-bar {
+  -webkit-app-region: drag;
+}
+
+.mac-desktop #items-title-bar input,
+.mac-desktop #items-title-bar button {
+  -webkit-app-region: no-drag;
+}
+
+.mac-desktop #editor-title-bar {
+  -webkit-app-region: drag;
+}
+
+.mac-desktop #editor-title-bar input,
+.mac-desktop #editor-title-bar button {
+  -webkit-app-region: no-drag;
+}
+
+.mac-desktop [data-dialog]::after {
+  content: '';
+  position: absolute;
+  top: 0;
+  left: 0;
+  width: 100%;
+  height: 36px;
   -webkit-app-region: drag;
 }
 
diff --git a/packages/desktop/package.json b/packages/desktop/package.json
index 2a030e56d..c1e882a4a 100644
--- a/packages/desktop/package.json
+++ b/packages/desktop/package.json
@@ -34,21 +34,21 @@
     "hoistingLimits": "workspaces"
   },
   "dependencies": {
-    "@electron/remote": "^2.0.9",
+    "@electron/remote": "^2.0.12",
     "@standardnotes/domain-core": "^1.34.1",
     "@standardnotes/electron-clear-data": "1.1.1",
     "@standardnotes/web": "workspace:*",
-    "axios": "^1.1.3",
-    "compare-versions": "^5.0.1",
+    "axios": "^1.4.0",
+    "compare-versions": "^6.1.0",
     "decrypt": "github:standardnotes/decrypt#master",
-    "dotenv": "^16.0.3",
-    "electron": "22.3.24",
+    "dotenv": "^16.3.1",
+    "electron": "27.0.0",
     "electron-log": "^4.4.8",
-    "electron-updater": "^5.3.0",
+    "electron-updater": "^6.1.4",
     "fs-extra": "^11.1.1",
     "lodash": "^4.17.21",
     "mime-types": "^2.1.35",
-    "mobx": "^6.7.0"
+    "mobx": "^6.10.2"
   },
   "devDependencies": {
     "@babel/core": "*",
diff --git a/yarn.lock b/yarn.lock
index 7e291a146..66e413ac6 100644
--- a/yarn.lock
+++ b/yarn.lock
@@ -2035,12 +2035,12 @@ __metadata:
   languageName: node
   linkType: hard
 
-"@electron/remote@npm:^2.0.9":
-  version: 2.0.10
-  resolution: "@electron/remote@npm:2.0.10"
+"@electron/remote@npm:^2.0.12":
+  version: 2.0.12
+  resolution: "@electron/remote@npm:2.0.12"
   peerDependencies:
     electron: ">= 13.0.0"
-  checksum: 74ab6fca7973f43d45e3372dc3bbd35552f63ba10f5673d08ec9d9fd06e74d5b2da696a9b297dae5baeaf5cd991fc65c4ee25582991f8c18316bd18ae1bed6a9
+  checksum: 63b5c729bb6c8c19e323016ea883a38ec1b8e5817ceba0faef9332e85252a4e5742b2ca5b41d7659714cce83698c5b122a6c7247edf3dbe9d031db60c8c91806
   languageName: node
   linkType: hard
 
@@ -4287,7 +4287,7 @@ __metadata:
   dependencies:
     "@babel/core": "*"
     "@babel/preset-env": "*"
-    "@electron/remote": ^2.0.9
+    "@electron/remote": ^2.0.12
     "@standardnotes/domain-core": ^1.34.1
     "@standardnotes/electron-clear-data": 1.1.1
     "@standardnotes/web": "workspace:*"
@@ -4298,17 +4298,17 @@ __metadata:
     "@types/proxyquire": ^1.3.28
     "@types/yauzl": ^2.10.0
     ava: ^5.1.0
-    axios: ^1.1.3
+    axios: ^1.4.0
     babel-loader: ^9.1.0
-    compare-versions: ^5.0.1
+    compare-versions: ^6.1.0
     copy-webpack-plugin: ^11.0.0
     decrypt: "github:standardnotes/decrypt#master"
-    dotenv: ^16.0.3
-    electron: 22.3.24
+    dotenv: ^16.3.1
+    electron: 27.0.0
     electron-builder: 23.6.0
     electron-log: ^4.4.8
     electron-notarize: ^1.2.1
-    electron-updater: ^5.3.0
+    electron-updater: ^6.1.4
     eslint: "*"
     eslint-config-prettier: ^8.9.0
     eslint-plugin-import: ^2.26.0
@@ -4318,7 +4318,7 @@ __metadata:
     fs-extra: ^11.1.1
     lodash: ^4.17.21
     mime-types: ^2.1.35
-    mobx: ^6.7.0
+    mobx: ^6.10.2
     prettier: "*"
     proxyquire: ^2.1.3
     rimraf: ^3.0.2
@@ -5726,10 +5726,10 @@ __metadata:
   languageName: node
   linkType: hard
 
-"@types/node@npm:^16.11.26":
-  version: 16.18.39
-  resolution: "@types/node@npm:16.18.39"
-  checksum: eac9b202b76013256cb517ca8d3e3f61df206edb1615ca8d8df4c80616e92879fe4d3f8570a11d60f4216a82724a3265d5888b24c6994c80b057a0423c9ff1d2
+"@types/node@npm:^18.11.18":
+  version: 18.18.4
+  resolution: "@types/node@npm:18.18.4"
+  checksum: 4901e91c4cc479bb58acbcd79236a97a0ad6db4a53cb1f4ba4cf32af15324c61b16faa6e31c1b09bf538a20feb5f5274239157ce5237f5741db0b9ab71e69c52
   languageName: node
   linkType: hard
 
@@ -5860,7 +5860,7 @@ __metadata:
   languageName: node
   linkType: hard
 
-"@types/semver@npm:^7.3.12, @types/semver@npm:^7.3.13, @types/semver@npm:^7.3.6, @types/semver@npm:^7.5.0":
+"@types/semver@npm:^7.3.12, @types/semver@npm:^7.3.13, @types/semver@npm:^7.5.0":
   version: 7.5.0
   resolution: "@types/semver@npm:7.5.0"
   checksum: 0a64b9b9c7424d9a467658b18dd70d1d781c2d6f033096a6e05762d20ebbad23c1b69b0083b0484722aabf35640b78ccc3de26368bcae1129c87e9df028a22e2
@@ -7410,14 +7410,14 @@ __metadata:
   languageName: node
   linkType: hard
 
-"axios@npm:^1.1.3":
-  version: 1.4.0
-  resolution: "axios@npm:1.4.0"
+"axios@npm:^1.4.0":
+  version: 1.5.1
+  resolution: "axios@npm:1.5.1"
   dependencies:
     follow-redirects: ^1.15.0
     form-data: ^4.0.0
     proxy-from-env: ^1.1.0
-  checksum: 7fb6a4313bae7f45e89d62c70a800913c303df653f19eafec88e56cea2e3821066b8409bc68be1930ecca80e861c52aa787659df0ffec6ad4d451c7816b9386b
+  checksum: 4444f06601f4ede154183767863d2b8e472b4a6bfc5253597ed6d21899887e1fd0ee2b3de792ac4f8459fe2e359d2aa07c216e45fd8b9e4e0688a6ebf48a5a8d
   languageName: node
   linkType: hard
 
@@ -8009,6 +8009,16 @@ __metadata:
   languageName: node
   linkType: hard
 
+"builder-util-runtime@npm:9.2.1":
+  version: 9.2.1
+  resolution: "builder-util-runtime@npm:9.2.1"
+  dependencies:
+    debug: ^4.3.4
+    sax: ^1.2.4
+  checksum: 6933e086b8ff9902cbd6d4c08d21d4a0437663ac849bc0939ec20a59cb2b084d7ab655c4dc2c71f854e77da152ff1f8e1240372665cb70e7b954afbfbf4d525a
+  languageName: node
+  linkType: hard
+
 "builder-util@npm:23.6.0":
   version: 23.6.0
   resolution: "builder-util@npm:23.6.0"
@@ -9008,10 +9018,10 @@ __metadata:
   languageName: node
   linkType: hard
 
-"compare-versions@npm:^5.0.1":
-  version: 5.0.3
-  resolution: "compare-versions@npm:5.0.3"
-  checksum: f66a4bb6ef8ff32031cc92c04dea4bbead039e72a7f6c7df7ef05f5a42ddca9202f8875b7449add54181e73b89f039662a8760c8db0ab036c4e8f653a7cd29c1
+"compare-versions@npm:^6.1.0":
+  version: 6.1.0
+  resolution: "compare-versions@npm:6.1.0"
+  checksum: d4e2a45706a023d8d0b6680338b66b79e20bd02d1947f0ac6531dab634cbed89fa373b3f03d503c5e489761194258d6e1bae67a07f88b1efc61648454f2d47e7
   languageName: node
   linkType: hard
 
@@ -10339,7 +10349,7 @@ __metadata:
   languageName: node
   linkType: hard
 
-"dotenv@npm:^16.0.3":
+"dotenv@npm:^16.0.3, dotenv@npm:^16.3.1":
   version: 16.3.1
   resolution: "dotenv@npm:16.3.1"
   checksum: 15d75e7279018f4bafd0ee9706593dd14455ddb71b3bcba9c52574460b7ccaf67d5cf8b2c08a5af1a9da6db36c956a04a1192b101ee102a3e0cf8817bbcf3dfd
@@ -10509,33 +10519,32 @@ __metadata:
   languageName: node
   linkType: hard
 
-"electron-updater@npm:^5.3.0":
-  version: 5.3.0
-  resolution: "electron-updater@npm:5.3.0"
+"electron-updater@npm:^6.1.4":
+  version: 6.1.5
+  resolution: "electron-updater@npm:6.1.5"
   dependencies:
-    "@types/semver": ^7.3.6
-    builder-util-runtime: 9.1.1
-    fs-extra: ^10.0.0
+    builder-util-runtime: 9.2.1
+    fs-extra: ^10.1.0
     js-yaml: ^4.1.0
     lazy-val: ^1.0.5
     lodash.escaperegexp: ^4.1.2
     lodash.isequal: ^4.5.0
-    semver: ^7.3.5
-    typed-emitter: ^2.1.0
-  checksum: 975381ffb0d9e17686f7f0b90739320922ca52d06ee548e89ceeb3b56bfc23180c20e7049e5c33ef789b228eb4c960c9886986e1332577866dca2437c315ed4e
+    semver: ^7.3.8
+    tiny-typed-emitter: ^2.1.0
+  checksum: 07d6cf1d3da0e6a9ed852777bb5acc73cc5bae250ffd5d20e0ddc674ae1856c675b37ea48fe0ae82445fedf033ce99d4836491fed9514d1085216a7f4fad42b8
   languageName: node
   linkType: hard
 
-"electron@npm:22.3.24":
-  version: 22.3.24
-  resolution: "electron@npm:22.3.24"
+"electron@npm:27.0.0":
+  version: 27.0.0
+  resolution: "electron@npm:27.0.0"
   dependencies:
     "@electron/get": ^2.0.0
-    "@types/node": ^16.11.26
+    "@types/node": ^18.11.18
     extract-zip: ^2.0.1
   bin:
     electron: cli.js
-  checksum: 28f0134e7e66ab8d89ec03059c759d9463ca1a2f5bac99069d1cbe18de78bb71dd4c29a63166456a46a701e62826fbf7533c754533b744965046012c4f220f68
+  checksum: 4a84cb894d5f626fe7a2b5171693e903ce82a7673aabc419e5d3d0d2f9cc8441e5088524ecd86a046beab4ba7dd13820b7a94c361c3e7bc2f0959d1a1a860df5
   languageName: node
   linkType: hard
 
@@ -17296,7 +17305,14 @@ __metadata:
   languageName: node
   linkType: hard
 
-"mobx@npm:^6.7.0, mobx@npm:^6.8.0":
+"mobx@npm:^6.10.2":
+  version: 6.10.2
+  resolution: "mobx@npm:6.10.2"
+  checksum: 14d6f1db4e3a61c823510ea130229c96bd4958b77d81057ac1abc6a439703eaf3ea2289192ef205b4250d3adb1d83a439ad56d5e53f2b967c6e62a6bccc23d8a
+  languageName: node
+  linkType: hard
+
+"mobx@npm:^6.8.0":
   version: 6.10.0
   resolution: "mobx@npm:6.10.0"
   checksum: 8279d5a978d845664fb1830ce1e7f3fcebd5809bd9be6f2cac9b190e07cf6f16b09581107cc2d1ff7097e979da758fefd9ac68db76c814b8e783e59d0b8e418c
@@ -20656,7 +20672,7 @@ __metadata:
   languageName: node
   linkType: hard
 
-"rxjs@npm:*, rxjs@npm:^7.5.5, rxjs@npm:^7.8.0":
+"rxjs@npm:^7.5.5, rxjs@npm:^7.8.0":
   version: 7.8.1
   resolution: "rxjs@npm:7.8.1"
   dependencies:
@@ -22453,6 +22469,13 @@ __metadata:
   languageName: node
   linkType: hard
 
+"tiny-typed-emitter@npm:^2.1.0":
+  version: 2.1.0
+  resolution: "tiny-typed-emitter@npm:2.1.0"
+  checksum: 709bca410054e08df4dc29d5ea0916328bb2900d60245c6a743068ea223887d9fd2c945b6070eb20336275a557a36c2808e5c87d2ed4b60633458632be4a3e10
+  languageName: node
+  linkType: hard
+
 "titleize@npm:^3.0.0":
   version: 3.0.0
   resolution: "titleize@npm:3.0.0"
@@ -22953,18 +22976,6 @@ __metadata:
   languageName: node
   linkType: hard
 
-"typed-emitter@npm:^2.1.0":
-  version: 2.1.0
-  resolution: "typed-emitter@npm:2.1.0"
-  dependencies:
-    rxjs: "*"
-  dependenciesMeta:
-    rxjs:
-      optional: true
-  checksum: 95821a9e05784b972cc9d152891fd12a56cb4b1a7c57e768c02bea6a8984da7aff8f19404a7b69eea11fae2a3b6c0c510a4c510f575f50162c759ae9059f2520
-  languageName: node
-  linkType: hard
-
 "typedarray-to-buffer@npm:^3.1.5":
   version: 3.1.5
   resolution: "typedarray-to-buffer@npm:3.1.5"