Mac Mail loses emails

About 6 months ago, I started noticing that a particular contractors emails I could NEVER receive (or even find) in Outlook (Mac 365). I could only find it if I searched it, but from tech support I found out search doesn't show you where the file is actually located.
DO have a system of filters that send the emails to different folders by project. But that doesn't seem to be the problem because I turned filters off and did it manually for several weeksand it still happened.
So I switched to Mac Mail Jan 1st and if anything the problem is a little bit worse. I am losing at least 2 per week (the ones I know about) and I'm just realizing its sending as well as receiving (even harder to realize unless someone tells you they never received something). The thing is, in MOST cases i can find them only if I do a search on my iphone. Provided they're recent, etc. I then tried switching from my company email addresses (which are POP accounts) to gmail which is imap and its still happening. I constantly need to search for things a year or more old for accounting work, etc. I think I've switched every variable I can think of, one at a time, and I've still got the same problem tho I've spent a **** ton of time and the tech support people at Apple don't even know as much as I've learned in a month.
I can switch back to outlook, but when you get email it give every email the CURRENT date, even if its from months ago, so that really ***** up the ability to search. I can say stop doing email on my iphone, but why if that's the only place I can find things? Does seem to be that getting email on my iphone is making it disappear elsewhere.
Any suggestion or resource much appreciated.

I'll assume you are using OS 10.6 Snow Leopard. (It helps if you post as much information about your set up as possible). Post here where those Mail gurus are:
https://discussions.apple.com/community/mac_os/mac_os_x_v10.6_snow_leopard#/?tag Set=1007

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We both use mac mail and have .me accounts.
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bingo123 wrote:
sorry gg30340 , Yes webmail works fine and I can receive from Outlook fine, just sent emails seems to disappear into a black hole from Outlook
Hi. Welcome to the forums.
For info, CP (Critical Path) has been in use for a few months now for the conversion from using Yahoo! mail servers.
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In the smtp setting, try removing @btinternet.com or @btopenworld.com from the username - despite what the online help might say.
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Mac Mail loses emails

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