OK, kept on playing with the files and got the problem go away.

The Outbox folder looked empty, but the Outbox file itself had all
messages since about September last year in it (54 MB to be precise).

-rw------- 1  54379156 2007-04-20 21:18 Outbox
-rw-r--r-- 1       124 2007-04-20 21:18 Outbox.cmeta
-rw------- 1     63806 2007-04-20 21:18 Outbox.ev-summary
-rw------- 1    345088 2007-04-20 19:34 Outbox.ibex.index
-rw------- 1    292504 2007-04-20 19:34 Outbox.ibex.index.data

I concatenated it and restarted Evolution. Sent a message, and killed
Evolution with -9. Restarted it. 

The first time round it did resend the messages sent since last restart,
but stopped thereafter, even after kill -9. I assume it automagically
healed those index pointer files after the first round or something?

Looks like you do not move data across files but only rearrange pointers
to it, and if something goes haywire due to disk overflow or other
reasons, strange things may happen in other folders as well?

I'd think that whenever Evolution thinks that Outbox is empty (i.e.
sending the messages was successful to all items found in there), it
should be safe to concatenate the related file, too? Would fix this
problem once and forever, maybe?

I hope these messages give enough clues to you guys to figure out the
inner details.

One humble request: for messages with multiple image attachments, how
about "View all attached images inline" option as one of the available
options?

Petri

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Evolution resends old mail after power failure
https://bugs.launchpad.net/bugs/64953
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