Mail Problem

Discussion of general issues, not related to a specific Mac or iDevice operating system.
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Richard Serkes
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Mail Problem

Post by Richard Serkes » Thu Jul 16, 2015 11:08 am

OK, I'm using Mac OS 10.10.4 with Mail v8.2. Everything is up to date.

Here's the problem... Yesterday I tried sending a weekly email to a group I work with. There are 79 recipients that I send to using Bcc: for reasons of privacy. I always send the email to myself in the To: field just to make sure the message goes through. When I sent the message it went out (or so I thought) but I didn't get my copy like I have in the past. So I called a member and asked that she check her INBOX and she hadn't received the message. However, it was in my SENT box suggesting that it had gone through. So then I tried using a different email client (Airmail v2.1) and got the same results. I found the message in my SENT folder but my copy never appeared in my INBOX.

Could the problem be with 79 recipients? Does my ISP think it is SPAM? So I divided the 79 into two groups one with 40 and one with 39. Again, no joy using both Mail and Airmail.

Then I thought that since I use a @.mac account with Apple that maybe Apple's email servers were wonky but the Apple site said all was good with a big green button. But just to try a different approach I sent things out through my Gmail account. Same results. The email wound up in my SENT folder but I never received my copy in my INBOX. And this was with Mail and Airmail. I also checked with my friend and she still hadn't received the email.

After tearing my hair out (figuratively, not literally) I gave up. But this morning I thought to myself, why not bypass my local email clients and/or any problems with the OS and go directly into the iCloud website and use the online email program. Everything worked just fine. The mail went out, I received my copy in my INBOX, and it appeared in the SENT folder. This tells me two things. (1) The 79 recipients wasn't the problem because if Apple thought this was SPAM it would have caught it online when I was in iCloud. (2) Something on my Mac is not right.

To that end I've booted to my clone and run Tech Tool Pro on the Macintosh HD repearing the volume structure, the directories, and even ran Repair Permissions. Nothing wrong with taking a shotgun approach I always say. I won't know if this will fix the problem until next week when I try to send out the weekly email but I was wondering if anyone has any insight or suggestions as to what's going on and how to fix it.

I've been sending out weekly emails to these people for a year and a half now with no problems so something has happened to my Mac within the last seven days.

Do I need to reload the OS which would give me an uncorrupted copy of Mail? But that doesn't make a lot of sense since both Mail and Airmail were doing the same thing. I think it's something else on the hard drive but I'm stumped.
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Stephen Hart
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Re: Mail Problem

Post by Stephen Hart » Thu Jul 16, 2015 5:54 pm

FWIW, here's my experience sending the SMUG monthly notice (from an e-mail to Jerry):

"I sent from my mac.com address, and the default sending server is iCloud. That failed.
Using my olympus.net server succeeded.
Spot checking, I received the notice. So did Jay."
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Richard Serkes
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Re: Mail Problem

Post by Richard Serkes » Thu Jul 16, 2015 7:13 pm

Stephen Hart wrote:FWIW, here's my experience sending the SMUG monthly notice (from an e-mail to Jerry):

"I sent from my mac.com address, and the default sending server is iCloud. That failed.
Using my olympus.net server succeeded.
Spot checking, I received the notice. So did Jay."
I'm not sure I understand what you're saying. Are you saying that the iCloud server is unreliable and I should use my Gmail account and therefore the Google server? But I tried that and the Google server also failed to send the email.

If it's my ISP then how could I use the online IMAP iCloud Mail program because I'd have to send the email via the ISP.

This is confusing and frustrating.
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Jay Cline
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Re: Mail Problem

Post by Jay Cline » Thu Jul 16, 2015 7:42 pm

It sounds like you did everything you possibly could to troubleshoot the problem.

If this all worked fine previously and nothing else has changed I'd suggest the likely temporary problem was with Quest being delayed at sending out the email. Might send out a test message to those same recipients to see what happens now.

Did you attempt to send the mail out with Gmail's webmail or do you just have a Gmail account in Mail?
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Richard Serkes
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Re: Mail Problem

Post by Richard Serkes » Thu Jul 16, 2015 8:11 pm

Jay Cline wrote:
Did you attempt to send the mail out with Gmail's webmail or do you just have a Gmail account in Mail?
I used my Gmail account in Mail and Airmail. It was when I logged in to my iCloud account online and used the IMAP online webmail app that I was able to get the message out.

So you think the hiccup was with Centurylink?
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Jay Cline
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Re: Mail Problem

Post by Jay Cline » Thu Jul 16, 2015 9:24 pm

It's my understanding that email goes to a server and is held until that server can send. Messages can get hung up just about anywhere along the line. Kind of like this:
Image

This explanation is even better because of the accent used.

https://youtu.be/g6NMFHuef6Y
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Richard Serkes
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Re: Mail Problem

Post by Richard Serkes » Thu Jul 16, 2015 9:48 pm

However (and I should have mentioned this earlier in this thread) while the mass email would not go through, emails to just one individual would go through. That's what made me think the 79 recipients was causing the problem. Some ISPs see that many recipients and assume the email is SPAM and won't send it. For that matter, when a single recipient's ISP sees that many other recipients the ISP assumes SPAM and won't let it go to the INBOX.

Bottom line, I've been doing this for we'll over a year and only yesterday did things go south.
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Stephen Hart
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Re: Mail Problem

Post by Stephen Hart » Fri Jul 17, 2015 9:13 am

I'm not sure I understand what you're saying. Are you saying that the iCloud server is unreliable and I should use my Gmail account and therefore the Google server? But I tried that and the Google server also failed to send the email.
The issue was with the outgoing mail server, not my account per se. For some reason, the iCloud outgoing mail server didn't work for the mass e-mail while my ISP did work.
"Design is not just what it looks like and feels like. Design is how it works."
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Richard Serkes
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Re: Mail Problem

Post by Richard Serkes » Fri Jul 17, 2015 9:19 am

Stephen Hart wrote:
I'm not sure I understand what you're saying. Are you saying that the iCloud server is unreliable and I should use my Gmail account and therefore the Google server? But I tried that and the Google server also failed to send the email.
The issue was with the outgoing mail server, not my account per se. For some reason, the iCloud outgoing mail server didn't work for the mass e-mail while my ISP did work.
OK, now I get it. But in my case since I was able to use the iCloud webmail program the iCloud server wasn't the problem. This suggests that something on my Mac or something between my Mac and the iCloud server was the culprit. I'll probably never know. But if I have this same problem next week then I have my work around and I'll reinstall OS 10.10.4 just in case there's a corrupted system file somewhere.
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Jay Cline
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Re: Mail Problem

Post by Jay Cline » Fri Jul 17, 2015 9:52 am

It appears that CenturyLink sets limits on the number of contacts you can send to, though it appears you came nowhere near that limit.
http://internethelp.centurylink.com/int ... imits.html
Email Size Limit: 20MB
'Send to' Limitations: 100 contacts
Webmail send limit: 100 per hour
SMTP send limit: 500 per hour
IP based email send limit: 50 per 5 minutes
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