P.S. I just got a new error message:

"Sending of the message failed. The message could not be sent because connecting to Outgoing server (SMTP) smtp-mail.outlook.com failed. The server may be unavailable or is refusing SMTP connections. Please verify that your Outgoing server (SMTP) settings are correct and try again."

Maybe that will shed some light on what's going on. Oh yeah and, while it would NOT send the message from my outlook account, I sent the same message from my Google Account in TBird and it sent right away.

Another P.S.

I forgot to mention my Outgoing server (SMTP) settings ARE correct. I sent an email from that very Outlook account USING those settings just a few hours earlier.

SMTP server 52.97.133.162

That is a very odd thing. Why are you specifying the server by IP address and not name? The IP address does appear to be somewhere in the MSN network (funny how all these years later internally they still have MSN even if the web site is outlook.com)

Is the IP address located in your SMTP server settings? or is it indicative of some sort of DNS issue.

Hi Matt. Don't understand your question. "...Why are you specifying the server by IP address and not name? " I just copied and pasted the error message that I get when it won't send the emails. I did look in the Server Settings and I see no IP address. Anyhow...

If the error message contains the IP address it is either in your settings or is a part of the problem

Could you please do the following:

1. Open the menu > Help > Troubleshooting Information, then click Copy text to Clipboard.
2. Go to https://pastebin.com and paste the info from your Troubleshooting Information page, then copy the resulting URL.
3. Open a reply to this post, and paste the link to your troubleshooting information.

Thanks for your help Matt. Here is the link: https://pastebin.com/S1MK6Guu

P.S. Don't know if this info will help but, the program worked fine for years before this happened sometime last year. But then, it was only with messages I sent as Replies. Now it happens (intermittently though) with all Outlook.com email messages. Seems to not have affected Gmail ones.

So, did you find anything Matt in my pastebin.com upload?

I have to say though, I'm a little surprised that this post hasn't gotten more replies from others in support. I see many posts from others getting this error messages (particularly the one about the incorrect greeting) and yet, there is no real solution. I've tried them all.

You have 18 accounts with outlook.com Fairly large number and given the strict rules forced on everyone about connection attempts I suggest you try changing to "get mail" frequency to 30 minutes and see if that causes a change.

I would also suggest you try removing anything that interferes with email sending (Probably anti virus). You are getting an error from an unresolved IP address. All your servers are addressed as FQN. So where is the bad redirect coming from?

My real guess is outlook.com has a bad configuration in a a server cluster and occasionally you get redirected to this broken machine. The domain name does belong in the MSN network, but it does not resolve in DNS which is an indicator your being send somewhere in outlook.com and should not receive visitors.

I appreciate your assessment Matt. Not aware of the strict rules. Can you point me to them?

Anyhow, my settings have been all along:

1) All email accounts set NOT to check at startup 2) Check for emails every 90 minutes. 2) And, accounts I don't use often are also unchecked so as NOT to check for emails every 90 minutes in an attempt to reduce activity.

I know. A lot of accounts (personal, business, multiple Youtube profile accounts, an expendable email account etc). The real mystery is that, I never had a problem sending mail or receiving mail until last August (2018). No settings changes, same amount of emails.

As far as Avast, I have "scan outgoing mail" unchecked. And the SSL thing is also unchecked. Don't know what else to do except uninstall the program but where do I go from there. I already got rid of AVG a few weeks ago thinking it was the problem.

You asked about the IP address error saying: "You are getting an error from an unresolved IP address. All your servers are addressed as FQN. So where is the bad redirect coming from? " How /where would I get the answer to that question about the bad redirect?

Server cluster? What is that? Broken Machine? Do you think I got hacked? Now I'm nervous too. heh heh. Was thinking of uninstalling TBird and reinstalling but, I'm worried I'll loose all my email addresses and have to add them all again one by one.

intanet said

Server cluster? What is that? Broken Machine?

A server cluster is just what it sounds like. say IMAP-outlook.com. It is not a single server but a cluster of them made to look like one to you and me, it might be two or three, but it is probably more like several shipping containers full of them distributed all around the world. Somewhere in the cluster is I suspect a broken machine, not the you will ever actually get through to anyone that knows anything at outlook. Like other big fish, they just proceed as if everything is Ok and your an idiot if it is not working for you. It is very rare for them to actually admit they had problem, but they are better than Yahoo.

Oh gosh, I know what you mean about them making you feel like an idiot and not fessing up to their messes. How many times they had me "jumping through hoops" to so called "troubleshoot" THEIR mess. So basically, are you saying that it's a problem on their servers and not on my computer or in Thunderbird? And, therefore, no fix? I was gonna uninstall/reinstall Thunderbird and, was just about to do some Googling about a safe way to do it without loosing all my accounts just before I got notified of your reply. So, it wouldn't be worth the effort then, if the problem is not with Thunderbird. Would you agree?

reinstall... It will not hurt, but I also doubt it will change anything as it is only a replacement of the program and the system integration components involved. Thunderbird stores setting and mail data separate to the program and does not remove them when you uninstall. So it is not an issue, just unlikely to be helpful.

Seriously it could be your end, but I am inclined to think the problem is the outlook end and leave it in the hopes one day the find the problem and fix it.

I agree, particularly since I can send Gmail out when this is happening with Outlook accounts. Well, thanks for saving me the trouble of trying an uninstall/reinstall. Spent enough time on this already. Take care, my friend. Annette