Hi, thanks for visiting Answer Desk! I'm Novie C.
7:31 pm
Novie C
Hi. How may I help you today?
7:32 pm
Me
Over the past few weeks I've experienced severe issues trying to use the email account for one of my companies (the only one hosted by Microsoft) over POP3 ( outlook.office365.com:995) or SMTP (smtp.office365.com:587). This is for my account kf@augusto.no using Thunderbird as the MUA.
7:32 pm
Me
Strangely it seems to work better with my Android phone or through the web UI, but debugging manually from three separate networks, e.g by doing a openssl s_client -starttls smtp -connect smtp.office365.com:587 I get a valid TLS hanshake but a timeout after the first EHLO showing "451 4.7.0 Timeout waiting for client input\nread:errno=0"
7:32 pm
Me
Similarly manual POP3 results in "-ERR Connection is closed. 12"
7:32 pm
Novie C
I see. I am glad that you have contacted Microsoft Answer Desk regarding this one.  Let me see what I can do for you.
7:34 pm
Novie C
Before we begin, allow me to properly document your case for future reference. May I have your email address and phone number please?
7:34 pm
Me
kf@augusto.no / +47 976 51 877
7:34 pm
Novie C
Thank you.
7:35 pm
Novie C
Are you using an Exchange Active Sync email account for this one Kristian?
7:36 pm
Me
no, we only have one exchange active sync accounts and that is used by a colleague of mine, so I use POP3 / SMTP
7:36 pm
Novie C
Okay. So how are you accessing this email account by the way? Are you using Office Outlook application for this one or just the webmail outlook.com through a browser?
7:38 pm
Me
This is all covered in the initial problem description, including the MUA used
7:38 pm
Hmm, okay. Based on the details you have provided me, I can say that this is an issue with the adding of a connected account to your Microsoft Account Kristian and it seems to be that this might be a possible setup/settings issue with the account but don't worry, we can check on this one now for us to see what is really happening.
7:42 pm
Before we move further, I’d like to provide you with some details on what you can expect from our chat today. We have a number of complimentary and Premium support options which I will explain depending on the severity and complexity of the issue. I may request to take control of your PC now but only with your permission. This will help in diagnosing as well as solving your issue depending on what service you choose.  Okay?
7:43 pm
Me
no, that is certainly not OK and that access will not be granted
7:44 pm
as for the connectivity issues, can you confirm that there are no general issues connecting with POP3 or SMTP to your datacenters?
7:44 pm
Me
in particular outlook.office365.com.g.office365.com. 300 IN CNAME outlook-emeawest2.office365.com.
7:45 pm
I understand your hesitation about the process of the remote access however in our situation right now, we will really need to check the user-end configurations of your account which is not available here in our end for us to properly identify the issue for you Kristian. And based on the status of the server, I am not seeing any problem and most of our customers are able to connect and use it properly. Also, there is no recent reported issue pertaining to the server settings that you have provided me earlier.
7:47 pm
POP3 config connects to outlook.office365.com on port 995 using SSL/TLS connection security and normal password authentication
7:49 pm
Me
SMTP use smtp.office365.com on port 587 with normal password auth and STARTTLS
7:49 pm
Yes, that is the correct configuration for the setup Kristian and since you are getting problem connecting the account using that settings, that means that there might be a possible user-end configuration of the account or might be a possible internal settings of the account which we can only diagnose by running a trace scan tools in the user's end. And for us to properly do that, what we need to do is to remotely access your device for us to execute that properly and make sure that we will be able to diagnose the issue for you correctly.
7:52 pm
The connection has worked properly before , the issue has just surfaced the past few weeks, and I can access it sporadically
7:53 pm
I understand. If you want, we can go ahead and start the remote access now for us to start running the trace diagnosis n your account for us to determine the root cause of this issue Kristian. If you are not confident using your work PC, maybe we can use other device(which don't contain any sensitive data) for us to access and start the trace from there in your account.
7:57 pm
I'm not confident giving Microsoft access to any of my data, which is why neither devices are running Microsoft , but GNU/Linux
Okay, I understand. No problem. If that is the case, then the best option that we have right now is to provide you some troubleshooting steps via email that you can use to check this issue in your end without the remote access. Is that okay with you?
8:00 pm
Me
Providing some steps to troubleshoot by email is fine, in particular if you describe the end result you want in case the commands needs translation for Unix
8:01 pm
I understand. I will do my best to provide you the equivalent command/process for Unix for this troubleshooting however, since we cannot cover entirely the Linux/GNU operating system, there might be steps that I will try to explain further so that you can easily translate it to Unix commands. If ever none of those troubleshooting steps works, please do contact us back here anytime for further assistance okay? We are 24/7 open to help.
8:06 pm