Why is Gmail (through Mac Mail) not sending some email messages?

May 12, 2008 8:34 PM

Help! Why is my Gmail, accessed through my Macbook's Mail application, occasionally not sending emails, even though they're listed as "sent"?

I recently learned that a prospective employer never received an important email I sent using Gmail through Mac's Mail-- I chalked it up as a fluke. Now I've learned that another person never received an email. I know that most of my emails have gone through without a problem. Three questions:

a) What is going on? All my messages are listed as "sent" in the Gmail "sent" folder-- but apparently some never *actually* got sent/received?

b) Is there any way to know which messages have/ have not been sent? I'm paranoid that many other emails have never been sent/received, but I have no way of knowing which ones.

c) Is there anything I can do to prevent this from happening in the future? Should I email everyone I've tried to email recently and ask if they've received my messages?

Thanks.

posted by airguitar2 to computers & internet (7 comments total)

I would expect that if they're in the sent folder on gmail (and not just in your local sent folder on the Mac) then it was actually sent out from gmail. Why it never arrived is a bit of a puzzle. Maybe these two recipients have over-zealous spam filters?

Do you connect to gmail from the Mac via POP or IMAP? If it's IMAP, I suppose it's possible that the Mail software on your Mac is saving it to gmail's sent folder, even though it wasn't actually sent.
posted by winston at 8:39 PM on May 12

I agree; the most likely reason is that they were auto-ashcanned at the receiving end.
posted by Class Goat at 9:00 PM on May 12

It's possible, even though you're on a Mac, that your IP address is blacklisted because of a spam-sending virus infection. This can happen if you share a connection with an infected PC, or if you are running Virtual PC or Parallels on your Mac and have an infected virtual machine (this is what happened to me).

This is the blacklist that many providers (inluding mac.com) use:

">http://cbl.abuseat.org/

You can check your status there. If your IP is blacklisted you'll need to remove the offending infected Windows installation from your network and fill in an application form to be deblacklisted, which happens pretty quickly.
posted by unSane at 9:15 PM on May 12

Being in the sent-mail folder is an indication only that your local mail client put it there over IMAP. The actual sending is not done by gmail, it's done by your local mailer using SMTP.

Because you claim to be sending from gmail but are not in the gmail IP block, it's quite possible that your mails have been discarded due to failing SPF or some other related check.

Or they got spamfiltered.
posted by polyglot at 2:41 AM on May 13

If your IMAP client is configured correctly for Gmail, it won't be copying Sent mails to the Sent folder; it will be letting Gmail do that, which it will do for any mails you send via smtp.gmail.com, which is the SMTP server you should be using for Gmail. So if you're sure they got into Sent because smtp.gmail.com put them there, the only way they would fail to reach their destinations is if those destinations discarded or spam-filtered them.

Some corporations actually do simply drop mails from Gmail addresses (along with mails from Hotmail and Yahoo) on the grounds that anybody using a free, public mail service is clearly a spammer; personally I think that's a brain-dead assumption, and would consider failing to land a job in such a corporation to be a stroke of good fortune. Life is too short to waste on pointy-haired bosses.
posted by flabdablet at 4:49 AM on May 13

unSane, that makes no sense; if airguitar2 is using Gmail, that blacklist has no effect whatsoever on his/her attempts to send mail unless Gmail itself is on the blacklist. In other words, that blacklist is for IP addresses of machines that are delivering a piece of mail to its final destination, not mail clients accessing webmail services. (And in other other words, when Mac.com uses that blacklist, it's for accepting mail from machines that are delivering it to users with mac.com email addresses, not for when it's accepting mail from authenticated users with mac.com email addresses who are sending mail outward.)

As for the core issue, I've run a slew of mail servers for a long time, and I agree with the prevailing sentiment here -- if the messages are in your Gmail sent folder, airguitar2, then they've successfully been sent by Gmail. The fact that they're not being received by their intended recipients is an issue at their end -- aggressive spam filters, something else similar -- and very, very unlikely to be a Gmail issue.

It all boils down to: you're assuming that because the emails weren't delivered into the recipients' inboxes, they weren't sent by Gmail, but that's an assumption that's way less likely to be true than the possibility that the mail systems at the recipients' ends interfered with the delivery of the messages to their inboxes. Given the existence of rock-solid authentication at the sending side of an email conversation, most mail hosts do precious little pre-processing of messages before putting them on the wire; given the lack of any real way to authorize and/or authenticate at the receivingend of an email conversation, nearly every mail host does a slew of pre-processing of messages before delivering them to their intended destinations.
posted by delfuego at 7:21 AM on May 13

It may make no sense to you but that's actually how mac.com mail works. I confirmed this with an Apple support person. My wife's mac.com mail was not getting sent, either from Mail.app or via the mac.com webmail page. It went to the sent box but never arrived anywhere.

It turns out that mac.com won't send mail that originates from an IP blacklisted by the CBL, whether or not the user is authenticated. It took me a long while and many blind alleys to figure this out because it DOES move the mail to the sent box but doesn't send it.

Yes, it's dumb. No, I don't know if gmail does the same thing. However it's a data point.

I was able to remove the IP address from the CBL and mac.com mail sending started working again.

Whenever you have mail delivery problems, check if you are on the CBL. It takes all of fifteen seconds and you are on the blacklist you need to get off it, whether or not it is the source of your mail woes.
posted by unSane at 7:14 PM on May 13