Transfers not Reflected in Transfer To Account

I have some transfers (like checking to savings, or checking to cash, etc) that don't show up in the other account, nor do they show up in a register report. I have ATMs that come out of my checking and should show as a transfer to my cash account, but when I look at the cash account, the transaction isn't there.
This may be related to how the downloaded transactions are recored. If from checking to savings, the bank download will just show a "transfer" in the category field, but if I fill in the correct t account, Quicken will say "I found a matching transaction. Would you like to connect it?". But with ATMs, there isn't a matching download transaction - so I manually enter the name of my cash account and hit enter. However, this transaction doesn't show up in my cash account, and the ATM doesn't show in my account transaction report that I do every month. I have to go back and delete the original one, and then re-enter an identical transaction - and THEN it shows up.
Answers
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I'm also having trouble with transfers. Recently I have to keep going back and trying to fix the transfers so the two-sides match. I wasn't having this problem until recently. I use the transfer to and select the correct account, but it loses the match. I have to keep going back and fixing them.
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Same issue, also recent.
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