diff --git a/apps/desktop/src/autofill/main/main-desktop-autotype.service.ts b/apps/desktop/src/autofill/main/main-desktop-autotype.service.ts
index 09f03d2ef8e..17c83b7e976 100644
--- a/apps/desktop/src/autofill/main/main-desktop-autotype.service.ts
+++ b/apps/desktop/src/autofill/main/main-desktop-autotype.service.ts
@@ -9,44 +9,44 @@ import { AutotypeKeyboardShortcut } from "../models/main-autotype-keyboard-short
 
 export class MainDesktopAutotypeService {
   autotypeKeyboardShortcut: AutotypeKeyboardShortcut;
+  private isInitialized: boolean = false;
 
   constructor(
     private logService: LogService,
     private windowMain: WindowMain,
   ) {
     this.autotypeKeyboardShortcut = new AutotypeKeyboardShortcut();
+
+    ipcMain.handle("autofill.initAutotype", () => {
+      this.init();
+    });
+
+    ipcMain.handle("autofill.autotypeIsInitialized", () => {
+      return this.isInitialized;
+    });
   }
 
   init() {
-    ipcMain.on("autofill.configureAutotype", (event, data) => {
-      if (data.enabled) {
-        const newKeyboardShortcut = new AutotypeKeyboardShortcut();
-        const newKeyboardShortcutIsValid = newKeyboardShortcut.set(data.keyboardShortcut);
-
-        if (newKeyboardShortcutIsValid) {
-          this.disableAutotype();
-          this.autotypeKeyboardShortcut = newKeyboardShortcut;
-          this.enableAutotype();
-        } else {
-          this.logService.error(
-            "Attempting to configure autotype but the shortcut given is invalid.",
-          );
-        }
+    ipcMain.on("autofill.toggleAutotype", (event, data) => {
+      if (data.enable) {
+        this.enableAutotype();
       } else {
         this.disableAutotype();
-
-        // Deregister the incoming keyboard shortcut if needed
-        const setCorrectly = this.autotypeKeyboardShortcut.set(data.keyboardShortcut);
-        if (
-          setCorrectly &&
-          globalShortcut.isRegistered(this.autotypeKeyboardShortcut.getElectronFormat())
-        ) {
-          globalShortcut.unregister(this.autotypeKeyboardShortcut.getElectronFormat());
-          this.logService.info("Autotype disabled.");
-        }
       }
     });
 
+    ipcMain.on("autofill.configureAutotype", (event, data) => {
+      const newKeyboardShortcut = new AutotypeKeyboardShortcut();
+      const newKeyboardShortcutIsValid = newKeyboardShortcut.set(data.keyboardShortcut);
+
+      if (!newKeyboardShortcutIsValid) {
+        this.logService.error("Configure autotype failed: the keyboard shortcut is invalid.");
+        return;
+      }
+
+      this.setKeyboardShortcut(newKeyboardShortcut);
+    });
+
     ipcMain.on("autofill.completeAutotypeRequest", (event, data) => {
       const { response } = data;
 
@@ -61,18 +61,30 @@ export class MainDesktopAutotypeService {
         );
       }
     });
+
+    this.isInitialized = true;
   }
 
-  disableAutotype() {
-    // Deregister the current keyboard shortcut if needed
+  // Deregister the keyboard shortcut if registered.
+  private disableAutotype() {
     const formattedKeyboardShortcut = this.autotypeKeyboardShortcut.getElectronFormat();
+
     if (globalShortcut.isRegistered(formattedKeyboardShortcut)) {
       globalShortcut.unregister(formattedKeyboardShortcut);
-      this.logService.info("Autotype disabled.");
+      this.logService.debug("Autotype disabled.");
+    } else {
+      this.logService.debug("Autotype is not registered, implicitly disabled.");
     }
   }
 
+  // Register the current keyboard shortcut if not already registered.
   private enableAutotype() {
+    const formattedKeyboardShortcut = this.autotypeKeyboardShortcut.getElectronFormat();
+    if (globalShortcut.isRegistered(formattedKeyboardShortcut)) {
+      this.logService.debug("Autotype is already enabled with the keyboard shortcut.");
+      return;
+    }
+
     const result = globalShortcut.register(
       this.autotypeKeyboardShortcut.getElectronFormat(),
       () => {
@@ -85,8 +97,31 @@ export class MainDesktopAutotypeService {
     );
 
     result
-      ? this.logService.info("Autotype enabled.")
-      : this.logService.info("Enabling autotype failed.");
+      ? this.logService.debug("Autotype enabled.")
+      : this.logService.error("Failed to enable Autotype.");
+  }
+
+  // Set the keyboard shortcut if it differs from the present one. If
+  // the keyboard shortcut is set, de-register the old shortcut first.
+  private setKeyboardShortcut(keyboardShortcut: AutotypeKeyboardShortcut) {
+    if (
+      keyboardShortcut.getElectronFormat() !== this.autotypeKeyboardShortcut.getElectronFormat()
+    ) {
+      const registered = globalShortcut.isRegistered(
+        this.autotypeKeyboardShortcut.getElectronFormat(),
+      );
+      if (registered) {
+        this.disableAutotype();
+      }
+      this.autotypeKeyboardShortcut = keyboardShortcut;
+      if (registered) {
+        this.enableAutotype();
+      }
+    } else {
+      this.logService.debug(
+        "configureAutotype called but keyboard shortcut is not different from current.",
+      );
+    }
   }
 
   private doAutotype(username: string, password: string, keyboardShortcut: string[]) {
diff --git a/apps/desktop/src/autofill/preload.ts b/apps/desktop/src/autofill/preload.ts
index fcb2f646743..4709b63cc26 100644
--- a/apps/desktop/src/autofill/preload.ts
+++ b/apps/desktop/src/autofill/preload.ts
@@ -127,8 +127,17 @@ export default {
       },
     );
   },
-  configureAutotype: (enabled: boolean, keyboardShortcut: string[]) => {
-    ipcRenderer.send("autofill.configureAutotype", { enabled, keyboardShortcut });
+  initAutotype: () => {
+    return ipcRenderer.invoke("autofill.initAutotype");
+  },
+  autotypeIsInitialized: () => {
+    return ipcRenderer.invoke("autofill.autotypeIsInitialized");
+  },
+  configureAutotype: (keyboardShortcut: string[]) => {
+    ipcRenderer.send("autofill.configureAutotype", { keyboardShortcut });
+  },
+  toggleAutotype: (enable: boolean) => {
+    ipcRenderer.send("autofill.toggleAutotype", { enable });
   },
   listenAutotypeRequest: (
     fn: (
diff --git a/apps/desktop/src/autofill/services/desktop-autotype.service.ts b/apps/desktop/src/autofill/services/desktop-autotype.service.ts
index 24ec3907a62..225307ea158 100644
--- a/apps/desktop/src/autofill/services/desktop-autotype.service.ts
+++ b/apps/desktop/src/autofill/services/desktop-autotype.service.ts
@@ -1,4 +1,14 @@
-import { combineLatest, filter, firstValueFrom, map, Observable, of, switchMap } from "rxjs";
+import {
+  combineLatest,
+  concatMap,
+  filter,
+  firstValueFrom,
+  map,
+  Observable,
+  of,
+  switchMap,
+  withLatestFrom,
+} from "rxjs";
 
 import { Account, AccountService } from "@bitwarden/common/auth/abstractions/account.service";
 import { AuthService } from "@bitwarden/common/auth/abstractions/auth.service";
@@ -18,6 +28,8 @@ import { CipherView } from "@bitwarden/common/vault/models/view/cipher.view";
 import { UserId } from "@bitwarden/user-core";
 
 import { DesktopAutotypeDefaultSettingPolicy } from "./desktop-autotype-policy.service";
+import { LogService } from "@bitwarden/logging";
+import { filterOutNullish } from "@bitwarden/common/vault/utils/observable-utilities";
 
 export const defaultWindowsAutotypeKeyboardShortcut: string[] = ["Control", "Shift", "B"];
 
@@ -46,8 +58,10 @@ export class DesktopAutotypeService {
     AUTOTYPE_KEYBOARD_SHORTCUT,
   );
 
+  // The enabled/disabled state from the user settings menu
   autotypeEnabledUserSetting$: Observable<boolean> = of(false);
-  resolvedAutotypeEnabled$: Observable<boolean> = of(false);
+
+  // The keyboard shortcut from the user settings menu
   autotypeKeyboardShortcut$: Observable<string[]> = of(defaultWindowsAutotypeKeyboardShortcut);
 
   constructor(
@@ -60,6 +74,14 @@ export class DesktopAutotypeService {
     private billingAccountProfileStateService: BillingAccountProfileStateService,
     private desktopAutotypePolicy: DesktopAutotypeDefaultSettingPolicy,
   ) {
+    this.autotypeEnabledUserSetting$ = this.autotypeEnabledState.state$.pipe(
+      map((enabled) => enabled ?? false),
+    );
+
+    this.autotypeKeyboardShortcut$ = this.autotypeKeyboardShortcut.state$.pipe(
+      map((shortcut) => shortcut ?? defaultWindowsAutotypeKeyboardShortcut),
+    );
+
     ipc.autofill.listenAutotypeRequest(async (windowTitle, callback) => {
       const possibleCiphers = await this.matchCiphersToWindowTitle(windowTitle);
       const firstCipher = possibleCiphers?.at(0);
@@ -72,66 +94,70 @@ export class DesktopAutotypeService {
   }
 
   async init() {
-    this.autotypeEnabledUserSetting$ = this.autotypeEnabledState.state$;
-    this.autotypeKeyboardShortcut$ = this.autotypeKeyboardShortcut.state$.pipe(
-      map((shortcut) => shortcut ?? defaultWindowsAutotypeKeyboardShortcut),
-    );
-
     // Currently Autotype is only supported for Windows
-    if (this.platformUtilsService.getDevice() === DeviceType.WindowsDesktop) {
-      // If `autotypeDefaultPolicy` is `true` for a user's organization, and the
-      // user has never changed their local autotype setting (`autotypeEnabledState`),
-      // we set their local setting to `true` (once the local user setting is changed
-      // by this policy or the user themselves, the default policy should
-      // never change the user setting again).
-      combineLatest([
-        this.autotypeEnabledState.state$,
-        this.desktopAutotypePolicy.autotypeDefaultSetting$,
-      ])
-        .pipe(
-          map(async ([autotypeEnabledState, autotypeDefaultPolicy]) => {
-            if (autotypeDefaultPolicy === true && autotypeEnabledState === null) {
-              await this.setAutotypeEnabledState(true);
-            }
-          }),
-        )
-        .subscribe();
-
-      // autotypeEnabledUserSetting$ publicly represents the value the
-      // user has set for autotyeEnabled in their local settings.
-      this.autotypeEnabledUserSetting$ = this.autotypeEnabledState.state$;
-
-      // resolvedAutotypeEnabled$ represents the final determination if the Autotype
-      // feature should be on or off.
-      this.resolvedAutotypeEnabled$ = combineLatest([
-        this.autotypeEnabledState.state$,
-        this.configService.getFeatureFlag$(FeatureFlag.WindowsDesktopAutotype),
-        this.accountService.activeAccount$.pipe(
-          map((activeAccount) => activeAccount?.id),
-          switchMap((userId) => this.authService.authStatusFor$(userId)),
-        ),
-        this.accountService.activeAccount$.pipe(
-          filter((account): account is Account => !!account),
-          switchMap((account) =>
-            this.billingAccountProfileStateService.hasPremiumFromAnySource$(account.id),
-          ),
-        ),
-      ]).pipe(
-        map(
-          ([autotypeEnabled, windowsDesktopAutotypeFeatureFlag, authStatus, hasPremium]) =>
-            autotypeEnabled &&
-            windowsDesktopAutotypeFeatureFlag &&
-            authStatus == AuthenticationStatus.Unlocked &&
-            hasPremium,
-        ),
-      );
-
-      combineLatest([this.resolvedAutotypeEnabled$, this.autotypeKeyboardShortcut$]).subscribe(
-        ([resolvedAutotypeEnabled, autotypeKeyboardShortcut]) => {
-          ipc.autofill.configureAutotype(resolvedAutotypeEnabled, autotypeKeyboardShortcut);
-        },
-      );
+    if (this.platformUtilsService.getDevice() !== DeviceType.WindowsDesktop) {
+      return;
     }
+
+    if (!(await ipc.autofill.autotypeIsInitialized())) {
+      await ipc.autofill.initAutotype();
+    }
+
+    // If `autotypeDefaultPolicy` is `true` for a user's organization, and the
+    // user has never changed their local autotype setting (`autotypeEnabledState`),
+    // we set their local setting to `true` (once the local user setting is changed
+    // by this policy or the user themselves, the default policy should
+    // never change the user setting again).
+    combineLatest([
+      this.autotypeEnabledState.state$,
+      this.desktopAutotypePolicy.autotypeDefaultSetting$,
+    ])
+      .pipe(
+        map(async ([autotypeEnabledState, autotypeDefaultPolicy]) => {
+          if (autotypeDefaultPolicy === true && autotypeEnabledState === null) {
+            await this.setAutotypeEnabledState(true);
+          }
+        }),
+      )
+      .subscribe();
+
+    // listen for changes in keyboard shortcut settings
+    this.autotypeKeyboardShortcut$
+      .pipe(
+        concatMap(async (keyboardShortcut) => {
+          ipc.autofill.configureAutotype(keyboardShortcut);
+        }),
+      )
+      .subscribe();
+
+    // listen for changes in factors that are required for enablement of the feature
+    combineLatest([
+      // if the user has enabled the setting
+      this.autotypeEnabledUserSetting$,
+      // if the feature flag is set
+      this.configService.getFeatureFlag$(FeatureFlag.WindowsDesktopAutotype),
+      // if there is an active account with an unlocked vault
+      this.authService.activeAccountStatus$,
+      // if the user's account is Premium
+      this.accountService.activeAccount$.pipe(
+        filter((account): account is Account => !!account),
+        switchMap((account) =>
+          this.billingAccountProfileStateService.hasPremiumFromAnySource$(account.id),
+        ),
+      ),
+    ])
+      .pipe(
+        concatMap(async ([settingsEnabled, ffEnabled, authStatus, hasPremium]) => {
+          const enabled =
+            settingsEnabled &&
+            ffEnabled &&
+            authStatus == AuthenticationStatus.Unlocked &&
+            hasPremium;
+
+          ipc.autofill.toggleAutotype(enabled);
+        }),
+      )
+      .subscribe();
   }
 
   async setAutotypeEnabledState(enabled: boolean): Promise<void> {
diff --git a/apps/desktop/src/main.ts b/apps/desktop/src/main.ts
index fbb83a1bf56..2a4c672d7b8 100644
--- a/apps/desktop/src/main.ts
+++ b/apps/desktop/src/main.ts
@@ -310,19 +310,6 @@ export class Main {
       this.logService,
       this.windowMain,
     );
-
-    app
-      .whenReady()
-      .then(() => {
-        this.mainDesktopAutotypeService.init();
-      })
-      .catch((reason) => {
-        this.logService.error("Error initializing Autotype.", reason);
-      });
-
-    app.on("will-quit", () => {
-      this.mainDesktopAutotypeService.disableAutotype();
-    });
   }
 
   bootstrap() {