I route both personal email (several addresses/aliases) and work email 
(just one address) to Gmail. I find it more efficient to have one 
destination for email, separating mail using approximately 25 filters 
developed over the past several years.

I occasionally get stung by two related problems, which I attribute to 
Gmail not considering the email address from which I am sending my message. 
Consider the following two examples. Assume my work email is [email protected]. 
I have lots of work.com addresses in my contacts, some of whose names 
overlap with non work addresses.

   1. I have a [email protected] contact and am also subscribed to the 
   [email protected] Google Group whose messages I receive by email. I 
   get a message at [email protected] and want to forward it to Bob. Because I 
   don't send mail to [email protected] as often as I correspond with other bike 
   geeks on [email protected], Gmail *always* selects the latter over 
   the former. Most of the time, when sending a message to Bob at work, I 
   remember this problem and correct it, either by typing an "@" or a space, 
   followed by the first letter of his last name, either of which eliminate 
   internet-bob as a possibility. Every once in awhile, I forget, however, and 
   work mail intended for Bob goes to internet-bob. Fortunately, the 
   internet-bob list/group rejects the messages I occasionally send there 
   because [email protected] is not a subscriber.
   2. I have another colleague at work, let's call him Jeff. Because I 
   communicate with Jeff both at work and outside work, I have both of his 
   work and Gmail addresses in my contact list. Most of the time I send Jeff 
   mail to his [email protected] address. I rarely send to his [email protected] 
   address. Still, every once in awhile, when I send a message to Jeff, the 
   Gmail auto-completer selects [email protected] as the recipient. I have no 
   idea why it does this only every-so-often.

Both of these mistakes would happen much less often if the auto-completer 
didn't get things right most of the time, lulling me into a false sense of 
security about the destination of my mail. I take full responsibility for 
inattentiveness in this area.

Still, it seems that if I am sending mail from my work.com address, 
auto-completion should prefer other work.com addresses over non-work 
addresses when I send mail. It should doubly prefer work.com addresses if I 
am replying to an email which was sent to  [email protected].

I hope the Gmail team is listening...

Thanks,

Skip

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