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ClintonLogan,
I don't remember PQ1 having the problem of missing entries (I have experienced this problem with PQ2 but it hasn't affected me financially). Is there not a way to set a "waiting" status on the transaction and leave it on the handheld?
I do see a potential problem with this issue (issue is probably the best word for it because it's not a bug or a software flaw). When recording what checks I've written without having the check number on hand, I like to use the "Next Check #" feature. If I have a transaction in the "waiting for acceptance" stack in Quicken and they don't show up in PQ, I may enter a double entry for a check #. I'm guessing this wouldn't be a major problem since I think Quicken won't accept the entry if it is a duplicate check #, but it is another issue.
ClintonLogan, I commend your for your desire to dive into user forums. It must be very similar to swimming with sharks ><^> 
You've made a great product. Keep up the great work and great Customer Service
- Burns
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