If I have multiple IRAs at Wealthsimple, does the tracking feature keep track of all my IRAs together?

Yes it does! Wealthsimple will calculate the remaining contribution room if you have multiple IRAs of the same type.

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How do I set up IRA contribution tracking?
Does the tracking feature take into account my contribution room including all my scheduled contributions?
If I have multiple IRAs at Wealthsimple, does the tracking feature keep track of all my IRAs together?
Does the tracking feature keep track of contributions to accounts outside of Wealthsimple?