I looked through imail logs and couldn't find where I tried to send the file from my exchange account to my imail account.
The first thing to do when trying to track down an issue like this (E-mails with .PDF files not being delivered) is to go through the log files. You might want to go to http://www.declude.com/info/logs.htm for an overview on reading the log files.
Essentially, the first step is to find all the IMail and Declude log file entries for an E-mail that got lost. Then, you check those entries to see what happened (an "ldeliver" or "rdeliver" line in the SMTP or SMTP- lines indicates that the E-mail was successfully delivered by IMail, which would usually mean the problem is on the client's end). If you see no SMTPD lines referring to the E-mail, then IMail never received it.
-Scott
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