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Not 100% sure. I have never clicked the "Bcc Myself" option. I guess this whole thing just baffles me since it works the proper way on my iPad, which I used the same steps and confirmed settings with the iPhone.. Goofy technology.

Hah..sorry. I was sending all those emails to myself just to test. Sorry about the confusion. I only see the sent messages in the sent box (unless I can catch them in the outbox). Maybe I just need to scrap the stock mail app and use the Gmail one, or something else. I just prefer how the...

I never thought of trying from one of the other 3 email addresses, so I tried last night. I got it to work with 1 of the others, but now, nothing. Very strange. When I attach them inline, they do send from any of the email addresses. This however, is the first time I have seen this. When...

Nope. Sorry. Thanks but that didn't work. However, it did ask me what size to send, which it hasn't for a LONG time. Also, after I wrote that post, I tried deleting the account completely, and reentering it, and that didn't help either..

I am currently running an iPhone 6 with iOS 8.1 with the mail app set up to use Gmail and multiple aliases. I used this website to set it up [redacted]. I also have the same exact set up running on a 2nd gen iPad, also running 8.1. My problem is, I can send mail perfectly fine all day on...