Choosing a membership plugin and living with it
Four plugins, four different shapes
MemberPress is the most all-in-one of the four: memberships, rules, coupons, reminders and reports live in one plugin, and its groups feature gives you upgrade paths without extra code. Paid Memberships Pro has an open-source core and a long list of add-ons, and developers find it easy to extend because so much of it runs through hooks. Restrict Content Pro is the leanest, a good fit when you want levels, restriction and Stripe without a large admin area. WooCommerce Memberships paired with WooCommerce Subscriptions makes sense when you already run a store, because a membership becomes something a product grants and members can get their own prices.
None is best everywhere. If you sell physical goods and memberships together, WooCommerce wins. If membership is the whole business and the team is not technical, MemberPress usually does. We say so before you buy anything.
Who holds the billing schedule
This detail decides how hard a future migration will be. With most Stripe setups in MemberPress, Paid Memberships Pro and Restrict Content Pro, the subscription itself lives at Stripe, and the site reacts to webhooks when an invoice is paid or fails. WooCommerce Subscriptions keeps the schedule on your site and charges a saved card when a renewal falls due. Both work. They fail differently: one depends on webhooks arriving, the other on scheduled actions running on time. We monitor whichever you have, and add a daily job that compares site records with the gateway so a missed event is caught and corrected.
Dunning is a design decision
When a renewal fails you have to choose: how many retries, over how many days, what the member is told, and whether access continues in the meantime. Gateways can retry on their own and the plugin can send reminders, but the two need to agree. A member who gets a "payment failed" email after the retry already succeeded will write to support. We set the retry schedule, the email sequence and the grace period as one flow and test it with the gateway's test cards that are built to decline.
Moving between membership plugins
A migration has two halves. The data half is mapping: users to levels, start and expiry dates, drip progress, coupons still in use. The money half is harder. Each active subscription has a customer and subscription reference at the gateway, and the new plugin has to recognize those references or take over the saved payment method. Where the old plugin left the schedule at Stripe and the new one runs its own, both will try to charge unless the old schedule is cancelled at the switch. We rehearse on a copy with the gateway in test mode, then compare member counts and next-renewal dates line by line. PayPal subscriptions are the awkward case, and sometimes the honest plan is to let them run on the old listener until they lapse. Our WordPress migration page covers the wider process.
Where custom development starts
Settings run out at rules the plugin authors never pictured: seats sold to a company and assigned by its admin, a level granted by a CRM field, access that depends on a credential held in another system, usage limits per member. We write those as a separate plugin on the membership plugin's own hooks, so updates stay routine. When the rules are the product, a Laravel SaaS build can be the cheaper thing to own, and we will tell you when you are near that line.