diff --git a/src/App/Services/BaseWatchDeviceService.cs b/src/App/Services/BaseWatchDeviceService.cs
index f2ffc0090..defd04a35 100644
--- a/src/App/Services/BaseWatchDeviceService.cs
+++ b/src/App/Services/BaseWatchDeviceService.cs
@@ -91,16 +91,19 @@ namespace Bit.App.Services
 
         private async Task<WatchState> GetStateAsync(string userId, bool shouldConnectToWatch)
         {
+            if (await _stateService.GetLastUserShouldConnectToWatchAsync()
+                &&
+                (userId is null || !await _stateService.IsAuthenticatedAsync()))
+            {
+                // if the last user had "Connect to Watch" enabled and there's no user authenticated
+                return WatchState.NeedLogin;
+            }
+
             if (!shouldConnectToWatch)
             {
                 return WatchState.NeedSetup;
             }
 
-            if (!await _stateService.IsAuthenticatedAsync() || userId is null)
-            {
-                return WatchState.NeedLogin;
-            }
-
             //if (await _vaultTimeoutService.IsLockedAsync() ||
             //    await _vaultTimeoutService.ShouldLockAsync())
             //{
diff --git a/src/Core/Abstractions/IStateService.cs b/src/Core/Abstractions/IStateService.cs
index 5f9b33e2d..f849c8178 100644
--- a/src/Core/Abstractions/IStateService.cs
+++ b/src/Core/Abstractions/IStateService.cs
@@ -162,5 +162,6 @@ namespace Bit.Core.Abstractions
         Task SetUsernameGenerationOptionsAsync(UsernameGenerationOptions value, string userId = null);
         Task<bool> GetShouldConnectToWatchAsync(string userId = null);
         Task SetShouldConnectToWatchAsync(bool shouldConnect, string userId = null);
+        Task<bool> GetLastUserShouldConnectToWatchAsync();
     }
 }
diff --git a/src/Core/Constants.cs b/src/Core/Constants.cs
index 4547ec091..9c0a4893c 100644
--- a/src/Core/Constants.cs
+++ b/src/Core/Constants.cs
@@ -36,6 +36,11 @@
         public const string NotificationData = "notificationData";
         public const string NotificationDataType = "Type";
         public const string PasswordlessLoginRequestKey = "passwordlessLoginRequest";
+        /// <summary>
+        /// This key is used to store the value of "ShouldConnectToWatch" of the last user that had logged in
+        /// which is used to handle Apple Watch state logic
+        /// </summary>
+        public const string LastUserShouldConnectToWatchKey = "lastUserShouldConnectToWatch";
         public const int SelectFileRequestCode = 42;
         public const int SelectFilePermissionRequestCode = 43;
         public const int SaveFileRequestCode = 44;
diff --git a/src/Core/Services/StateService.cs b/src/Core/Services/StateService.cs
index 9b7371f55..1390cf351 100644
--- a/src/Core/Services/StateService.cs
+++ b/src/Core/Services/StateService.cs
@@ -84,6 +84,8 @@ namespace Bit.Core.Services
             // Update pre-auth settings based on now-active user
             await SetRememberedOrgIdentifierAsync(await GetRememberedOrgIdentifierAsync());
             await SetPreAuthEnvironmentUrlsAsync(await GetEnvironmentUrlsAsync());
+
+            await SetLastUserShouldConnectToWatchAsync();
         }
 
         public async Task CheckExtensionActiveUserAndSwitchIfNeededAsync()
@@ -1708,6 +1710,21 @@ namespace Bit.Core.Services
                 ReconcileOptions(new StorageOptions { UserId = userId }, await GetDefaultStorageOptionsAsync());
             var key = Constants.ShouldConnectToWatchKey(reconciledOptions.UserId);
             await SetValueAsync(key, shouldConnect, reconciledOptions);
+            await SetLastUserShouldConnectToWatchAsync(shouldConnect);
+        }
+
+        public async Task<bool> GetLastUserShouldConnectToWatchAsync()
+        {
+            var options = await GetDefaultStorageOptionsAsync();
+            var key = Constants.LastUserShouldConnectToWatchKey;
+            return await GetValueAsync<bool?>(key, options) ?? false;
+        }
+
+        private async Task SetLastUserShouldConnectToWatchAsync(bool? shouldConnect = null)
+        {
+            var options = await GetDefaultStorageOptionsAsync();
+            var key = Constants.LastUserShouldConnectToWatchKey;
+            await SetValueAsync(key, shouldConnect ?? await GetShouldConnectToWatchAsync(), options);
         }
     }
 }
diff --git a/src/watchOS/bitwarden/bitwarden WatchKit Extension/ViewModels/CipherListViewModel.swift b/src/watchOS/bitwarden/bitwarden WatchKit Extension/ViewModels/CipherListViewModel.swift
index 0cafc784e..13402ecc4 100644
--- a/src/watchOS/bitwarden/bitwarden WatchKit Extension/ViewModels/CipherListViewModel.swift	
+++ b/src/watchOS/bitwarden/bitwarden WatchKit Extension/ViewModels/CipherListViewModel.swift	
@@ -51,12 +51,6 @@ class CipherListViewModel : ObservableObject {
         
         user = StateService.shared.getUser()
         
-        if user == nil && !watchConnectivityManager.isSessionActivated {
-            currentState = .needSetup
-            showingSheet = true
-            return
-        }
-        
         currentState = state ?? StateService.shared.currentState
         showingSheet = currentState != .valid