diff --git a/src/Umbraco.Infrastructure/Security/BackOfficeUserStore.cs b/src/Umbraco.Infrastructure/Security/BackOfficeUserStore.cs
index ade3ca7d1c..244885887e 100644
--- a/src/Umbraco.Infrastructure/Security/BackOfficeUserStore.cs
+++ b/src/Umbraco.Infrastructure/Security/BackOfficeUserStore.cs
@@ -440,15 +440,22 @@ public class BackOfficeUserStore : UmbracoUserStore<BackOfficeIdentityUser, Iden
 
         IIdentityUserToken? token = user.LoginTokens.FirstOrDefault(x =>
             x.LoginProvider.InvariantEquals(loginProvider) && x.Name.InvariantEquals(name));
-        if (token == null)
+
+        // We have to remove token and then re-add to ensure that LoginTokens are dirty, which is required for them to save
+        // This is because we're using an observable collection, which only cares about added/removed items.
+        if (token is not null)
         {
-            user.LoginTokens.Add(new IdentityUserToken(loginProvider, name, value, user.Id));
-        }
-        else
-        {
-            token.Value = value;
+            // The token hasn't changed, so there's no reason for us to re-add it.
+            if (token.Value == value)
+            {
+                return Task.CompletedTask;
+            }
+
+            user.LoginTokens.Remove(token);
         }
 
+        user.LoginTokens.Add(new IdentityUserToken(loginProvider, name, value, user.Id));
+
         return Task.CompletedTask;
     }
 
diff --git a/src/Umbraco.Infrastructure/Security/MemberUserStore.cs b/src/Umbraco.Infrastructure/Security/MemberUserStore.cs
index db19da026e..40bfc73a3d 100644
--- a/src/Umbraco.Infrastructure/Security/MemberUserStore.cs
+++ b/src/Umbraco.Infrastructure/Security/MemberUserStore.cs
@@ -580,15 +580,22 @@ public class MemberUserStore : UmbracoUserStore<MemberIdentityUser, UmbracoIdent
 
         IIdentityUserToken? token = user.LoginTokens.FirstOrDefault(x =>
             x.LoginProvider.InvariantEquals(loginProvider) && x.Name.InvariantEquals(name));
-        if (token == null)
+
+        // We have to remove token and then re-add to ensure that LoginTokens are dirty, which is required for them to save
+        // This is because we're using an observable collection, which only cares about added/removed items.
+        if (token is not null)
         {
-            user.LoginTokens.Add(new IdentityUserToken(loginProvider, name, value, user.Id));
-        }
-        else
-        {
-            token.Value = value;
+            // The token hasn't changed, so there's no reason for us to re-add it.
+            if (token.Value == value)
+            {
+                return Task.CompletedTask;
+            }
+
+            user.LoginTokens.Remove(token);
         }
 
+        user.LoginTokens.Add(new IdentityUserToken(loginProvider, name, value, user.Id));
+
         return Task.CompletedTask;
     }