How to test office365 smtp is working?

Mark M · 21 Nov 2014 at 11:38

We use some software that needs to send email via SMTP but when I set the details up it comes back with an error to say the connection to the server has failed. A gmail email address works fine so its something to do with exchange/365.

Is there anyway I can test to see if its the program or 365 causing the problem? We connect to the Exchange server with outlook which has always worked fine.

Could there be a firewall or port issue with the draytek router?

Any other suggestions appreciated thanks.

Mark M · 21 Nov 2014 at 12:26

The software seems fairly limited and just comes back with "connection failed"

Mark M · 21 Nov 2014 at 14:19

I couldnt work out telnet or blat but tried another smtp sender and using exactly the same details it sent an email no problem so I have to assume that its the program thats the problem?

Mark M · 26 Nov 2014 at 10:50

It only has the option to put in your email and password, smtp server etc.

Mark M · 26 Nov 2014 at 13:03

Thank you both for the replies, I will read the technet article later on this evening.

I had a look on the mxtoolbox websiter and ran a mx lookup for the smtp server that office 365 have provided - smtp.office365.com and it returns the following results:

ype Domain Name Canonical Name
CNAME outlook.office365.com lb.geo.office365.com
CNAME smtp.outlook.office365.com outlook.office365.com
CNAME smtp.office365.com smtp.outlook.office365.com

I have been entering the smpt details as smtp.office365.com into the software but the above Cname comes back as smtp.outlook.office365.com. Could hat be anything?

Mark M · 26 Nov 2014 at 13:37

In the settings there is a check box for "Use SSL/TLS" - which I have selected but also tried without.

The settings from the web access are as follows:

Pop setting
Server name: outlook.office365.com
Port: 995
Encryption method: SSL

IMAP setting
Server name: outlook.office365.com
Port: 993
Encryption method: SSL

SMTP setting
Server name: smtp.office365.com
Port: 587
Encryption method: TLS

Thanks again for your help

EDIT - The software asks for the following:

Host - smtp.office365.com
Port - 587
Use SSL/TLS - yes
Username - I assume this is just my email address?
Password - double checked
Senders email - my email

Mark M · 26 Nov 2014 at 14:26

Ive had a look through the program folder and the roaming app folder and cant see anything that relates to an email log. I'll give them a call and see if they can point me in the right direction.

Mark M · 26 Nov 2014 at 14:32

Theyve asked me to send the developer an email so will let you know what they come back with.

The network is pretty simple. All computers plug into the same switch which is connected to a Draytek Vigor 2920n (which has a fixed IP from the business centre I am in) Maybe it would be worth checking another internet connection in another room that doesnt have a fixed IP perhaps?

Mark M · 26 Nov 2014 at 15:41

Thanks I will look into the router exception.

No, all computers have a dynamic IP issued by the router but the router has a fixed external IP address for the internet (not sure of correct terminology but basically I can access the router/network remotely from that IP address)

Mark M · 26 Nov 2014 at 16:35

Caged said:
Just whitelist the public IP and don't bother with authentication. Use your firewall to control access to outbound SMTP so you don't get a client relaying through your mail server.

I will also look into the IP whitelist. Are there any specific articles I can look at that?

visibleman said:
If you've tried an 'SMTP sender' app and it worked then i'd assume it's something to do with Moneysoft Payroll Manager rather than Office365 or the Draytek - infact, i've used the exact same setup, 2920n and using a Office365 account's SMTP, for router/server/software notifications in a few locations without issue.

I'd double check the Office365 account in a email app using the SMTP settings and see if it'll send mail and similarly it might be worth setting up a dummy GoogleMail/Hotmail/Yahoo/simple mail account on web hosting/etc account and seeing if Moneysoft Payroll Manager will send mail using the dummy account.

Could I use something like thunderbird to test the smtp settings?

Ive set up a temp gmail account which works fine with the Payroll software but not sure if office365 could have an issue with the 2920n whereas the gmail account doesnt?

Mark M · 27 Nov 2014 at 12:44

Set up the SMTP Relay....and it works!

You guys are the best! Please stand in line for virtual hugs and kisses!