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I have been two days now trying to figure out how to help myself and my clients, and I just can't figure it out.
We are trying to send smtp email from various addresses/domains hosted at mediatemple to various addresses/domains hosted on office 365 and the mails always bounce back with
Server error: '550 relay not permitted'
to the sender account - but absolutely no useful information is included, no copy of the original mail we sent, no header to look at as no mail to look at, and no way from the office 365 accounts that I can find to review the mail that was returned.
I've been studying and trying to learn all about spf records and have tried dozens of attempts to set one that will finally satisfy office 365 to accept the emails I am sending but either this is completely unrelated to the problem or else I just flat out need to find another way to try and make a living because I must be the worst IT Consultant to every walk the earth - I can't figure it out.
I sure hate when I look so stupid in front of the clients I brought to Office 365
Thanks for the feedback.
I think you might be barking up the wrong tree... Assuming I am reading your problems correctly:
-You have trouble sending e-mail from terriffic.it to anywhere (Office 365, Yahoo, Gmail)
-You do not have e-mail service hosted by your ISP (Mediatemple?)
-You are getting a non-helpful "550 relay not permitted error"
A 550 error (and man, I have not seen one of those in a long time) usually happens when you try to use an SMTP server that you do not have permissions to send through. Back in the day... (WAAAAY back in the day), SMTP servers used to allow anyone to send e-mail through them unauthenticated, until Spammers took advantage of that loophole. Now most ISP's force you to authenticate as an authorized user before they will relay your e-mail. If you are not doing so, they'll give you that 550 error.
You can read more here (the topic was written in 2003, but still applies: office.microsoft.com/.../troubleshoot-550-553-and-relay-prohibited-errors-HA001112833.aspx)
If I had to guess, the 550 error is coming from whoever owns the SMTP server you are trying to send through (MediaTemple?), as whatever user you are trying to send from does not have permissions on that SMTP server to send e-mail. It sounds like you have called your ISP (which isn't hosting your e-mail) and are posting to this forum (which isn't receiving your e-mail)... Have you called MediaTemple to ask why you can't send e-mail through their server?
NDR messages from the Office 365 servers usually have lots of information in the headers... I would guess your e-mail is never making it that far.I don't think the SPF record has anything to do with it :)
Just my guess.
BTW... try running some of the tests here: www.testexchangeconnectivity.com. They can help point out some common problems sending/receiving e-mail (it tests SMTP servers, checks to see if your server is blacklisted, has the SPF records setup correctly, etc.) Maybe it will help.
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So for example I am sitting here on a coxbusiness broadband line trying to send email from firstname.lastname@example.org on mediatemple to email@example.com on office 365.
I have set the spf record at mediatemple for terrific.it to a dozen different things, but I can't be allowed to send any email to office 365 accounts
According to your description, I understand that users cannot send emails to email addresses on the Office 365, and the sender will receive Non Delivery Reports (NDR).
Could you provide the entire NDR? It will help us further troubleshoot this issue, and you can hide the sensitive information, such as important email address.
And I'd like to confirm the following things:
1. Can you receive emails from other domain using Office 365 mailbox?
2. Can you send emails to other domain using the address hosted on mediatemple?
3. If this issue only occurs when sending SMTP email from domains hosted at mediatemple, do you use your own SMTP server or the Office 365 SMTP server?
We want to narrow down whether it is a separate issue between these two domains (terrfic.it hosted on mediatemple and Office 365).
I have used Office 365 for quite a while, and receive lots of email from lots of people.
When I use the webmail client at mediatemple to send mail from firstname.lastname@example.org to say, email@example.com then it works. Mail arrives.
When I use my outlook client to send the same mail, using the smtp server mediatemple provides, I get a non-delivery message from "System Administrator" which is frustrating because:
-it does not indicate which system administrator
-it has no header information
-it says there is an attachment, but there is not or the attachment is null, in other words there is no copy of the original sent message with its header info to troubleshoot anything from.
-the message says:
Your message did not reach some or all of the intended recipients.
Sent: 5/19/2013 11:28 PM
The following recipient(s) cannot be reached:
David E Wadleigh on 5/19/2013 11:28 PM
Server error: '550 relay not permitted'
Which is a nice way to give a spammer the bum's rush, but not helpful for a legitimate sender to troubleshoot the problem.
I have verified, I thought, my outlook client settings as I can send email to myself ie to firstname.lastname@example.org from email@example.com using the outlook client, and also the setup passes the outlook test message, and also I have lots of experience with setting up the outlook client properly. However, after writing this sentence I just tried and find I can't send email to my accounts at gmail.com or yahoo.com either so obviously the problem is at mediatemple or my office.
I have been struggling with setting up an effective SPF record in the DNS for terrific.it but I can't tell if I am making progress or not, largely because none of the messages I get back give me any header info or copies of the failed message so I have nothing but a bunch of 550 relay errors to troubleshoot with. I did make some progress, as when I started I couldn't even send email with the webmail interface but now I can after setting an SPF record.
My ISP goes "Oh, well you don't host your email here so too bad so sad we can't help you, call your email administrator" Man, I miss the days when you could just send email and get email, before all these spammers forced us to make things so complicated I can't even get through the securitymeasures to email my own self now.
Yes on barking up the wrong tree. The trouble with being a one man band is often that you have nobody to talk to about your troubles, and sometimes you just don't see what you are doing wrong until you verbalize your twisted thought process for someone else to question.
I had trouble with my Outlook Client. For whatever reason, I was still able to send and receive email to the media temple hosted email accounts, and send and receive the outlook test message you get when you set up the email account in outlook. This had me convinced that the Outlook client was configured correctly and working properly, but now I see that this was not the case.
I rebooted, never hurts when its not Linux, and reentered the password for SMTP authorization in the Outlook client. Now it works fine. Publicly humbled again, but I needed it. Thanks.