diff --git a/libs/angular/src/auth/guards/redirect.guard.ts b/libs/angular/src/auth/guards/redirect.guard.ts
index 0c43673c34..760558dfb5 100644
--- a/libs/angular/src/auth/guards/redirect.guard.ts
+++ b/libs/angular/src/auth/guards/redirect.guard.ts
@@ -6,6 +6,7 @@ import { AuthService } from "@bitwarden/common/auth/abstractions/auth.service";
 import { DeviceTrustServiceAbstraction } from "@bitwarden/common/auth/abstractions/device-trust.service.abstraction";
 import { AuthenticationStatus } from "@bitwarden/common/auth/enums/authentication-status";
 import { CryptoService } from "@bitwarden/common/platform/abstractions/crypto.service";
+import { LogService } from "@bitwarden/common/platform/abstractions/log.service";
 
 export interface RedirectRoutes {
   loggedIn: string;
@@ -32,6 +33,7 @@ export function redirectGuard(overrides: Partial<RedirectRoutes> = {}): CanActiv
     const authService = inject(AuthService);
     const cryptoService = inject(CryptoService);
     const deviceTrustService = inject(DeviceTrustServiceAbstraction);
+    const logService = inject(LogService);
     const router = inject(Router);
 
     const authStatus = await authService.getAuthStatus();
@@ -49,6 +51,12 @@ export function redirectGuard(overrides: Partial<RedirectRoutes> = {}): CanActiv
     const tdeEnabled = await firstValueFrom(deviceTrustService.supportsDeviceTrust$);
     const everHadUserKey = await firstValueFrom(cryptoService.everHadUserKey$);
     if (authStatus === AuthenticationStatus.Locked && tdeEnabled && !everHadUserKey) {
+      logService.info(
+        "Sending user to TDE decryption options. AuthStatus is %s. TDE support is %s. Ever had user key is %s.",
+        AuthenticationStatus[authStatus],
+        tdeEnabled,
+        everHadUserKey,
+      );
       return router.createUrlTree([routes.notDecrypted], { queryParams: route.queryParams });
     }
 
diff --git a/libs/angular/src/auth/guards/tde-decryption-required.guard.ts b/libs/angular/src/auth/guards/tde-decryption-required.guard.ts
index 524ce7dce5..51d1a5a3b5 100644
--- a/libs/angular/src/auth/guards/tde-decryption-required.guard.ts
+++ b/libs/angular/src/auth/guards/tde-decryption-required.guard.ts
@@ -11,6 +11,7 @@ import { AuthService } from "@bitwarden/common/auth/abstractions/auth.service";
 import { DeviceTrustServiceAbstraction } from "@bitwarden/common/auth/abstractions/device-trust.service.abstraction";
 import { AuthenticationStatus } from "@bitwarden/common/auth/enums/authentication-status";
 import { CryptoService } from "@bitwarden/common/platform/abstractions/crypto.service";
+import { LogService } from "@bitwarden/common/platform/abstractions/log.service";
 
 /**
  * Only allow access to this route if the vault is locked and has never been decrypted.
@@ -23,15 +24,30 @@ export function tdeDecryptionRequiredGuard(): CanActivateFn {
     const authService = inject(AuthService);
     const cryptoService = inject(CryptoService);
     const deviceTrustService = inject(DeviceTrustServiceAbstraction);
+    const logService = inject(LogService);
     const router = inject(Router);
 
     const authStatus = await authService.getAuthStatus();
     const tdeEnabled = await firstValueFrom(deviceTrustService.supportsDeviceTrust$);
     const everHadUserKey = await firstValueFrom(cryptoService.everHadUserKey$);
+
+    // We need to determine if we should bypass the decryption options and send the user to the vault.
+    // The ONLY time that we want to send a user to the decryption options is when:
+    // 1. The user's auth status is Locked, AND
+    // 2. TDE is enabled, AND
+    // 3. The user has never had a user key in state since last logout.
+    // The inverse of this is when we should send the user to the vault.
     if (authStatus !== AuthenticationStatus.Locked || !tdeEnabled || everHadUserKey) {
       return router.createUrlTree(["/"]);
     }
 
+    logService.info(
+      "Sending user to TDE decryption options. AuthStatus is %s. TDE support is %s. Ever had user key is %s.",
+      AuthenticationStatus[authStatus],
+      tdeEnabled,
+      everHadUserKey,
+    );
+
     return true;
   };
 }
diff --git a/libs/auth/src/common/login-strategies/sso-login.strategy.ts b/libs/auth/src/common/login-strategies/sso-login.strategy.ts
index b7ed8906e7..2ba0f682b5 100644
--- a/libs/auth/src/common/login-strategies/sso-login.strategy.ts
+++ b/libs/auth/src/common/login-strategies/sso-login.strategy.ts
@@ -87,12 +87,16 @@ export class SsoLoginStrategy extends LoginStrategy {
 
     data.userEnteredEmail = credentials.email;
 
+    const deviceRequest = await this.buildDeviceRequest();
+
+    this.logService.info("Logging in with appId %s.", deviceRequest.identifier);
+
     data.tokenRequest = new SsoTokenRequest(
       credentials.code,
       credentials.codeVerifier,
       credentials.redirectUrl,
       await this.buildTwoFactor(credentials.twoFactor, credentials.email),
-      await this.buildDeviceRequest(),
+      deviceRequest,
     );
 
     this.cache.next(data);
@@ -195,12 +199,18 @@ export class SsoLoginStrategy extends LoginStrategy {
 
     // Note: TDE and key connector are mutually exclusive
     if (userDecryptionOptions?.trustedDeviceOption) {
+      this.logService.info("Attempting to set user key with approved admin auth request.");
+
+      // Try to use the user key from an approved admin request if it exists.
+      // Using it will clear it from state and future requests will use the device key.
       await this.trySetUserKeyWithApprovedAdminRequestIfExists(userId);
 
       const hasUserKey = await this.cryptoService.hasUserKey(userId);
 
-      // Only try to set user key with device key if admin approval request was not successful
+      // Only try to set user key with device key if admin approval request was not successful.
       if (!hasUserKey) {
+        this.logService.info("Attempting to set user key with device key.");
+
         await this.trySetUserKeyWithDeviceKey(tokenResponse, userId);
       }
     } else if (
@@ -275,11 +285,27 @@ export class SsoLoginStrategy extends LoginStrategy {
   ): Promise<void> {
     const trustedDeviceOption = tokenResponse.userDecryptionOptions?.trustedDeviceOption;
 
+    if (!trustedDeviceOption) {
+      this.logService.error("Unable to set user key due to missing trustedDeviceOption.");
+      return;
+    }
+
     const deviceKey = await this.deviceTrustService.getDeviceKey(userId);
     const encDevicePrivateKey = trustedDeviceOption?.encryptedPrivateKey;
     const encUserKey = trustedDeviceOption?.encryptedUserKey;
 
     if (!deviceKey || !encDevicePrivateKey || !encUserKey) {
+      if (!deviceKey) {
+        await this.logService.warning("Unable to set user key due to missing device key.");
+      }
+      if (!encDevicePrivateKey) {
+        await this.logService.warning(
+          "Unable to set user key due to missing encrypted device private key.",
+        );
+      }
+      if (!encUserKey) {
+        await this.logService.warning("Unable to set user key due to missing encrypted user key.");
+      }
       return;
     }