DNS problem trying to ping or send email using smtp-mail.outlook.com after upgrade to 17.10

After upgrading to Ubuntu 17.10, I find I am unable to send emails using the confusingly named Outlook (i.e. what used to be Hotmail) SMTP server.

When I try to ping the hostname smtp-mail.outlook.com I get

ping: smtp-mail.outlook.com: Name or service not known

However when I try nslookup smtp-mail.outlook.com I get

Server: 127.0.0.53
Address: 127.0.0.53#53
Non-authoritative answer:
smtp-mail.outlook.com canonical name = smtp.live.com.
smtp.live.com canonical name = smtp.glbdns2.microsoft.com.
smtp.glbdns2.microsoft.com canonical name = smtp.office365.com.
smtp.office365.com canonical name = smtp.outlook.office365.com.
smtp.outlook.office365.com canonical name = outlook.office365.com.
outlook.office365.com canonical name = lb.geo.office365.com.
lb.geo.office365.com canonical name = outlook.office365.com.g.office365.com.
outlook.office365.com.g.office365.com canonical name = outlook-emeawest2.office365.com.
Name: outlook-emeawest2.office365.com
Address: 40.101.4.18
...

I have looked around on various other questions about DNS problems in Ubuntu and tried a couple of things but as far as I can see, everything appears to be in order. I can also ping other internet addresses, it seems to be just this one that is having trouble.

This was working fine before I upgraded.

Any suggestions?

2 Answers

I'm having the same problem, using systemd-resolved. LP bug reported:

A workaround is to look up an IP address for it from the command line using "host", then add it to your /etc/hosts file:

host smtp-mail.outlook.com
[choose IP_ADDRESS for the command below from one reported here]
sudo /bin/bash -c 'echo "IP_ADDRESS smtp-mail.outlook.com" >> /etc/hosts'

I have the same problem to ping smtp-mail.outlook.com on my Notebook with Debian Stretch. I am able to ping the address from another computer with Debian Jessie. There I could find out that both smtp-mail.outlook.com and imap-mail.outlook.com point to outlook-emeacenter.office365.com, sometimes as well to outlook-emeacenter3.office365.com, outlook-emeacenter4.office365.com, etc. These seems to change all the time. My current workaround solution is that I set up my mail program (evolution) with outlook-emeacenter5.office365.com as incoming mail server and outlook-emeacenter3.office365 as outgoing mailserver and everything seems to work fine. It is more a trial-and-error solution, but the best I could get running so far.