Its an age old question and I am none the wiser. I think I shall let you decide after reading my recent experience with Mail.app and Gmail.
I have recently developed an insatiable interest in encryption algorithms and have been fooling around with the excellent open source implementation i,e GPG and its accompanying plugin for Mail.app on OS X. I installed the requisite packages and created a key pair. My problem was that I did not have anybody to send encrypted email to!!, so I decided to send one to who else but myself.
I composed this email in Mail.app and sent it from my Gmail account to my ( the same ) Gmail address. Funnily enough I never got this mail. The mail was definitely sitting in my inbox when I checked using the Gmail interface. Mistaking the encryption process as the culprit I sent another email, this time unencrypted and that too was never downloaded by Mail.app. The mail did show up in my inbox however!
Intrigued, I posted this problem on the Apple discussion lists and got this reply from a very helpful person who calls himself David Gimeno Gost. I have reproduced the text of the discussion verbatim below which you can also read here.
I have 2 Gmail addresses and have been retrieving mail from them via POP, using Mail.app for a while now. I am using OS 10.4.6
Of late I noticed a problem that I haven’t seen before. It is as such. If I send an email using Mail.app with the same “From” and “To” gmail address and later try and download that email using Mail.app, that email is never downloaded using POP, though I can see it in my inbox using the web interface. Please note that this particular condition needs to be satisfied i.e, the email needs to be sent and received to the same Gmail address. Mail.app is able to receive emails if sent from one Gmail address to the other and if sent from the web interface, even if from the same account!!
I am able to receive email sent to my gmail addresses everyday and Mail downloads them without any problem. It is only the above stated case that seems to be confusing. I have correctly configured Mail.app to receive Gmail as I am able to download may emails from various people everyday.
Any help is appreciated.
David Gimeno Gost :
Gmail POP access does not work as a normal POP mail server would. I’ve added another case to the explanation I usually give about how Gmail works to take your problem into account:
1. Messages downloaded by any POP mail client are marked as downloaded at the server, and no longer available to either the same or any other mail client.
2. To make already downloaded Gmail messages available for POP access again, you must log into your Gmail account with a web browser and re-enable POP downloading for all your messages, which will cause everything (and I mean everything) still there to be downloaded again.
3. Any “Remove copy from server” account settings in Mail > Preferences > Accounts > Advanced have absolutely no effect on the messages stored on the server. The reason is that, after being downloaded, those messages are no longer available to any mail client, not even to the same client that has just downloaded them, not even for deleting them or checking whether they are still there.
4. Messages created and sent using the web interface will be downloaded by your POP mail client as if they were incoming messages. You can set up a rule in Mail to automatically route those messages to the appropriate Sent mailbox (or to any other mailbox for that matter) if that’s what you want. Although this may seem weird, it’s good because it allows archiving all messages locally in Mail, regardless of how they were sent — as long as you don’t access the same Gmail account with more than one mail client, that is.
5. Messages created and sent using a POP mail client such as Mail are also treated as if they were incoming messages for POP purposes, just as in 4. What prevents them from being downloaded is that Gmail marks them as already downloaded immediately. They would, however, be downloaded if Gmail settings were changed as described in 2 above.
Your problem seems to be that Gmail doesn’t actually create a copy of your message in order to send it to yourself. Rather, it simply treats the message as any other incoming message but, since it’s already been marked as downloaded, Mail cannot see it. I believe this is an oversight on Gmail’s part (i.e. a bug). You may want to contact them and ask for them to fix the problem.
You can imagine how thrilled I was at having found a bug in Gmail!!
I was all set to report it and was trawling through Googles Help Center, when I was absolutely shocked to find that the Google team seemed to know about this bug and have clearly documented it for people who had difficulties with POP access! The text of which is as follows;
Help Center Home > POP Access
Did you try sending a message to yourself?
When you send a message to your Gmail account from your POP client, you won’t receive a copy. However, messages you send to your Gmail address from your Gmail account will arrive in your inbox if you are the only recipient.
I am not quite sure whether I am reading too much into this, and would like to know whether this has been the experience of other Gmail users out there?
Do let me know!
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