@bfittes1:
Yes, your reading of the "Received:" headers is correct.
Note one thing that should make your head hurt. It shows a sent time of 08:32:44, and an initial received time of 08:30:23.
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That's very simple: some of the computers do not have their time synchronized. Based on the combination of the facts, I'd conclude it is likely the computer that generated the e-mail. Note, that whatever is in the "Date:" header is essentially written by the program that created that message (e-mail client for e-mails sent by a person, an automated script/program for some mass-mailings like that). And in principle, they can write there whatever time they want.
As for your sorting/viewing of the time/date:
There are essentially (at least) three different times associated with the message:
1. "Date:" header formed by the mailer
2. The last (topmost) "Received:" header that is formed by the last SMTP server in the chain.
3. The time of when the IMAP server noticed the message in the Inbox (or any other mailbox, if on-server filtering/sorting is enabled). This can be IMAP-server dependent.
I am not 100% sure, but based on Kostya's comment and what is written in the FAQ under the item "Messages out of order, or wrong message dates" (Did you read it, as Kostya suggested?)
http://www.aqua-mail.com/?page_id=227 , - I'd say Aquamail is using #3 for the "received" time.
And as that FAQ answer describes, a number of things can affect that "received" time.
Additionally, from Kostya's remark, I suspect that Aquamail looks at that "received" time only once, when it downloads the message. (I.e. the setting for the time doesn't have retroactive force.)
From your description, I am not completely sure if you restore the messages from the backup, or they get downloaded each time. If you are restoring the entire database with the messages that have been downloaded by Aquamail, then the originally "recorded" time for the message (per Aquamail) is probably used in the sorting regardless of your setting.
HTH.