Because Trello's model is deliberately narrow - boards, lists, cards, labels, checklists, due dates, and attachments - it is unusually easy to adopt, and the first decision when replacing it is whether to keep that exact shape or move to something with milestones, custom fields, and reporting built in. The catch is schema discipline: Trello lets teams improvise with card text and Power-Ups, which hides process inside conventions, so a replacement should make that structure explicit enough to report on and back up. PLANKA and WeKan keep the familiar board, while Plane trades some simplicity for cycles, modules, and analytics once a board has become real project infrastructure.
Expect the gaps around polish, integrations, and operations rather than the board itself. Trello's mature drag-and-drop, notifications, mobile apps, and large Power-Up marketplace are hard to match one for one, and open source options tend to be stronger on control but weaker on no-code automation, calendar sync, or email-to-card flows. Self-hosting also means you inherit email delivery, file storage, authentication, upgrades, and backups, so a tool that shines in a demo can still fail if reminders or attachments are unreliable for your team.
Migration usually starts with Trello's own export. Individual boards come out as JSON that preserves much of the structure - lists, cards, descriptions, labels, checklists, due dates, members, comments, and activity - but how much survives depends on the importer on the other side. Vikunja is worth a look here because it ships a built-in Trello importer, which shortens the most tedious part. Attachments often need separate handling, and Power-Up data, automation rules, custom fields, watchers, and votes usually require cleanup. Run a test import on one representative board, map users and labels deliberately, freeze the old board during cutover, and keep the export as a permanent audit copy.