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I am tweaking our current user journey for adding specific items to your 'favourites' list.

The question is: if the user isn't logged in when they add an item to their 'favourites' - should they be prompted to log in at that point?

Or should they be allowed to add more items until they click checkout and then be prompted to log in then?

I feel it would be less disruptive to what the user expects if they need to log in after clicking 'Checkout' then being prompted. But then my concern is if the users don't click checkout and the session ends. They could potentially lose their items.

cottingham
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Make it as painless as possible, do not request login when users are still exploring products.

Some articles:

Shopping Cart or Wishlist? Saving Products for Later in Ecommerce

The shopping cart is not only a place to store items until purchase: it is a comparison table, a reference, a scrapbook for ideas. Thus, contrary to the modern ecommerce teams’ beliefs, adding an item to a shopping cart doesn’t necessarily mean that the item has a high chance of being purchased right away. People often use the shopping cart as a tool to help them make purchasing decisions, and the shopping cart is as much a sandbox for consideration of products as it is a direct means to purchase. Keep that in mind if you’re tracking shopping-cart abandonment as one of your analytics metrics: an item left in the shopping cart may actually be leading to a purchase later on.

Users often wish to purchase only some of their cart’s contents right away, but don’t want to lose all the work that went into finding other products of interest. Provide an easy-to-find feature to save items for later, label it something else than “wishlist,” and don’t block access to it with login walls.

Login Walls Stop Users in Their Tracks

As a rule of thumb, we recommend that you use the reciprocity principle when considering a login wall in front of your users. Always weigh in what the perceived benefits are for the users: if there is the slimmest chance that those benefits are not evident, forego the login wall — either all together or by pushing it to the point where users are convinced of the logic behind it and know exactly what to expect from your site.

Nicolas
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Never ask a user to sign in when they are in the exploratory phase of shopping - this is a big barrier to entry.

Encourage them to add favourites to a wishlist/shopping cart and then they will have motivation to save later.

Don't be concerned about the data being lost - there are a number of ways the data can be stored/maintained until they have signed in/up.