Trying to start new but fills are all messed up

Starting January 1, 2025, I began entering my expenses again. I deleted everything before then, to start completely over. I entered my assets (bank and CC accounts). I didn’t do any envelope fills because I was trying to figure out what my monthly expenses were.
On March 31, I figured out the amounts I should fill my envelopes with, and did a fill April 1.
May 1 I did the monthly fill. But I am so confused. E.g. for groceries my fill is $250. But on the Fill Envelopes page, it says the fill was $1449.88. Same for every envelope. The chart on the left is accurate but the “check register” shows a much larger fill.
Why is this and am I doing anything wrong?
Thank you for any advice.

It’s hard to tell without a screenshot, but it sounds like your envelopes were deeply in the red since you’d been spending without filling. When you finally filled the envelopes, you had to make up for all the spending you’ve done so far and then add the current budget on top of that. From now on your fills should be closer to what you expect. Would that explain it?

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Um, probably? What if I retroactively “filled” the envelopes from when I re-started?

You could certainly do that to keep things neat, or alternately just move the money from Available to the envelopes now all at once (especially since today is the 1st!)
Your ledger will show those envelopes in the red until the Fill, but it doesn’t sound like that was the primary benefit of the app for you anyway. Just be sure that today each envelope has a full month’s worth of spending to draw from, if you can, so that you can see whether you’re staying within your budget in real time. Don’t dip into the red in Available to fill them though, or you’ll risk spending money you don’t have/overdrawing your account.