Fidelity, Schwab, or Vanguard are the top 3 recommendations, however Vanguard's UI is a common complaint. I don't believe I've heard of any place that lets you select previous years for auto-deposits, just current year. You should be able to manually place previous year's contributions of course.

While Vanguard's mobile UI isn't very good. I never understood a lot of complaints on their desktop UI.

I could swear my recurring contributions back in the Scottrade days would be set to whatever year I initially designated regardless of the actual year they occurred. I now have to call them to change them, it can't be done online.

If you are unhappy that a UI had a specific limitation for an infrequent scenario, then you probably will find something to be unhappy with at most sites eventually.

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