Mail won't send but Connection Doctor says smtp account OK.

Hi Roger,

Just wanted to let you know that you're not alone in possible self-inflicted grief. 🙂 I was having this same problem today and your authentication tip did the trick. So thanks very much!

J

I've just gotten back to work after a 2 week break and I also can't send email anymore. I've trashed preferences, re-created my account etc. and when that didn't work I applied the 10.5.6 combo updater as well as the December 22 mail updater. The email system at work is imap based. I can receive emails from anywhere, I can send emails to anyone here at work but I cannot send emails outside work (like to my home address for example) even though my co-workers using imap can. I've tried creating a new account with and without setting authentication and nothing works. This all used to work before my 2 week break (back when my world was 10.5.5) and all my email SMTP settings are (still) the same as my co-workers.

I'm dead in the water here - I'm highly reluctant to open a ticket to our IS department because they don't want anything to do with Macs. I'm 99% sure this is a Mac problem.

HELP!! (please...)

Mick,

It sounds like during the period you were absent, an IP address was changed or some other action to fully qualify the SMTP was not completed to allow sending to outside domains. This is likely not a Mac or Mail problem, other than network recognition in the same way as your colleagues. Sometimes this happens when a static IP address is required. Have you had your Mac away from the network during your absence?

This is the result of some filter guard mechanism on your company SMTP.

Ernie

Message was edited by: Ernie Stamper

Hi Ernie,

I take my Mac to use at home at the end of every work day and bring it back to work every morning. I did have it at home during those 2 weeks off. I figured it probably wouldn't be a network thing because I currently can browse the web, receive emails and even send email within the company walls. It's only sending emails outside the company that isn't working. Do you still think it's something to do with the company's SMTP setup?

I'm in the same boat. I'm back at work after a 5day weekend, but mail won't work with my accounts. Furthermore, ichat, and certain internet radio stations won't load. I talked to the IT group who says they've done nothing in the last week. All the PC's seem to be working.

Greetings folks! Ernie, I'm NOT intending to argue, but I really don't think your proposal has anything to do with the issue. Like the others, I have the same problem. It started perhaps late mid-November or early December; I can't remember. It happened OUT OF THE BLUE. I haven't had my MacBook away from the network, no settings were changed on it, and no modifications with the ISP. My ISP is bluewin.ch (Im in Switzerland). I can send an e-mail to anyone who in the bluewin domain with no problems. I cannot send a message to anyone (including my University account or gmail) outside of the bluewin network. What is particularly interesting is, of the three accounts that I have setup in Mail, only my bluewin account is not functioning. I can receive messages, but not send from it.

I've spent hours on the phone with Apple support (not U.S. Apple support). They even had me do a capture data thing and they said it looked fine. They're confident that this is with the ISP. The ISP says that it's not their problem because with a Mac on their end they can send messages... even with my account info.

Before calling Apple support, I spent some time searching on these forums and discovered that many other people are having the same issue and it started LONG before me. From what I figured out based on those topics, this trouble started when Apple made the change with the outgoing server ports. They created two options: default (25, 465, 587) and a second option for a custom port. Before that revision of Mail, it doesn't seem as though people had problems.

The solutions that I have read that have worked for some people are:
1. Try turning on the SSL even if it's not required by your ISP
2. Use the custom port option and put in the one required even it's listed in the option above.

But now I think the MOST IMPORTANT thing is for anyone having this problem, PLEASE PLEASE PLEASE, call Apple Support! Doing so will show them that this problem is not just a few isolated cases. Once they see that more people are calling in with this problem, they will really need to fix it. And by the way, I had (and still have) this problem before and after the 10.5.6 update.

Message was edited by: rminot

I have a zillion applications running while at work. Do you know if between these preference setting tweaks that I can see the new results right away, or do I have to quit and restart Mail, or do I have to restart the whole machine?

No my friend. _That's the joy of a Mac!_ Yippe! No need to restart. You should be able to make all the changes you want to your smtp servers without even needing to quit mail. In fact, when I was doing all these things with Apple support, I never restarted.

The only time they had me restart, was at the beginning of all this to reset the P-RAM. Doing so is easy and does no harm. You can do that too if you like. When you restart (or boot-up) your computer, as soon as you hear the bong, hold down CMD-OPTION-P-R until you hear the second bong.

Good luck. And PLEASE, if what you're trying doesn't work, call Apple Support. We're never going to get out of this mess until they know more people have this problem.

Hi,

What I proposed to Mick is very specific, and very narrow in application. Probably has nothing to do with your issue, but I will review. If Mick's SMTP can be used to send to those addresses in his same domain, then it is not a problem with how the SMTP is set up. I have seen his issue before!

Ernie

So I've tried all combinations (but didn't zap the PRAM because I can't do a restart yet) and nothing worked. So it seems to me that you're disagreeing with the previous post that says it's most definitely my company's SMTP that's screwed up. As it turns out, they did do some network maintenance over the break, but everything's working fine for all my non-Mac co-workers on IMAP (I'm the only guy with a Mac here).

Doh! Now I think I'm confused. Previously you said:

Yes! If Mail and your Mac can send to in-house domain addresses but not those from other domains, then it is almost certainly an issue with the SMTP and spam guards.

but now you say:

If Mick's SMTP can be used to send to those addresses in his same domain, then it is not a problem with how the SMTP is set up. I have seen his issue before!

So are you saying that my Mail preferences are correctly setup and someone in our corporate IS department screwed up something in their SMTP configuration over the break? If so, what will they say to me when everybody else using the IMAP email (most have PCs running exchange mail) is not having a problem? They are highly likely to say it's a Mac problem because I'm the only one affected. Pretty hard to fault that logic...

Mick,

The set-up within Mail to send to the in-house domain addresses with the corp SMTP is the same as when sending to addresses for all domains. The SMTP can review any address it is being asked to send to, and refuse -- this is a function not related to Mail or set-up of the SMTP, and is meant to prevent unauthorized use of the corp SMTP for sending SPAM.

When a SMTP can be used from more than one location, such as remotely, often there is a safeguard to verify the location as being trustworthy. One method is to have a static IP address, which may even include the connection path. It is my opinion that your IT dept has implemented such a safe guard in some manner. If you simply tell them that you can send to in house addresses and not those belonging to other domains, they should recognize this is a problem not Mac specific, and not hide behind that excuse.

How do you connect to the LAN -- cable or wireless? If cable, try another computer in the same connection and see if it can send.

Ernie

Message was edited by: Ernie Stamper

I connect to the LAN via ethernet. Our company has only two kinds of computers - PC laptops (all using exchange mail) and big stationary linux based workstations with static IPs that use IMAP email and should never be disconnected from the network. And then there's lonesome me with my Mac who does NOT have a static IP because my machine is unsanctioned (but they turn a blind eye to it's usage). I've only worked here for about 3 months and this last 2 week absence is the longest I've had the Mac off the network.

So it sounds like you're saying the SMTP has convinced itself that my current IP address is not sanctioned and that's why I'm the only one affected. Therefore if I get them to fix this (somehow) then I'm only doomed to have a repeat performance some random time later. Does that sound about right?

Mick,

I think your last paragraph pretty well sums it up.

Could it be that while you were gone, they approved (perhaps reapproved) each port where a computer (laptop) was connected to the LAN as a sanctioned IP address, but since you were not there and connected, you were forgotten? Can you have someone with a PC laptop connect to your ethernet cable and check whether they can still send?

Ernie

Greetings! It's morning over here in Switzeland. Now I'm very interested in these latest developements! Ernie, perhaps Mick's problem and mine are different. But, from what he says, they sound alike to me. I'm no newbie to computer troubleshooting, but I am new when it comes to complicated networking issues. Where Mick and I differ is that I am not on a company network (I'm a monk in a monastery), I connect wirelessly. And, since I'm a monk, I haven't been anywhere. My laptop has not been off the network. So,there's no chance of what you suggest about authenticating IP addresses and being missed. Our network is very small, and everyone (except for printers) use DHCP. One day I could send messages, the next day I can't.

Basically our network is setup like you would have a network setup in your house: nothing complicated. Internet comes in from an ISP: bluewin, and is then redistributed via a router and a few wireless access points. We don't have an SMTP.

So, what then would you suggest be a solution to my problem? I can send messages to anyone who has an address at bluewin.ch. With Apple Support, I setup a gmail account that works fine. But I fear that sooner or later the same problem will arise and then I'll really be stuck. Also, the account that I have with the University works fine too. It's only the bluewin one that does not allow me to send outside of its network.

I completely agree that something has happened and that it's an authentication problem with the SMTP, but the ISP refuses to believe that, and Apple says everthing works fine.

And now I'm stuck in the middle.... and I know I'm not alone. That being the case, it certainly seems as though this is something special with the Mac because it happens to other people with different ISP's.

Thoughts?