Configure Outbound email with Office 365

[it_support]

Hi All,

I have an issue setting up outbound email with Office 365 SMTP client submission protocol.
Can anybody assist?

My code is as follow:
# Outbound Email Configuration
#————-
mail.from.default=test@mydomain.com.sg
mail.host=smtp.office365.com
mail.port=587
mail.username=test@mydomain.com.sg
mail.password=XXXXX
mail.protocol=smtps
mail.smtps.starttls.enable=true
mail.smtps.auth=true


##### Test SMTP setup
mail.testmessage.send=true
mail.testmessage.to=test@mydomain.com.sg
mail.testmessage.subject=Alfresco SMTP Test
mail.testmessage.text=This is to inform you that Afresco services have just started, caused either by manual restart or by the backup scripts.


Can anyone guide me to resolve the issue? I am using Alfresco Community v4.0.0

Thanks in advance.

[borisstankov]

Hello there,

Did you tried to capture the traffic between both systems (alfresco <–> smtp server) if alfresco asks correctly to login and use the server and how the server rejects it?

Maybe you didn't put the options in the correct way.

Regards!

[it_support]

Hi Boris,

How to captured the traffic?
Are you sure that Alfresco did trigger the SMTP?

could you guide me which options to put in the correct way?

Thanks.

[borisstankov]

OK, that's basic troubleshooting for connection between the two server.

Make sure that you can ping the smtp server from the alfresco server.
Then you need to check if you cna use the telnet command on the same port 587.

telnet smtp.server 587
‍‍‍

IF you get connected then you have the access to the system on that port from the alfresco server.
Now we are sure that everything from network point of view is OK.

Now you need to use tcpdump in order to generate a .pcap file if your alfresco server is running on linux, if not you need wireshark (for example) in order to catch the trafik: https://www.wireshark.org/download.html
Use as destination the smpt server IP address and as source the IP of the alfresco. When you have setup this. You need to restart the alfresco service and check the trafik.
IF you need more assistance for the wireshark or for the tcpdump command, please refer on the net how to use them.
Keep in mind that all .pcap files cna be opened with wireshark and it is in user readable format, because it's decrypts the packets between the two hosts.

[mrogers]

Before you resort to wireshark (not that that is not good advice.) 

Basics first,  Have you any error messages in your alfresco log file?  I'd expect there to be details there.

[borisstankov]

Well, yes. I'll do the same, but I thought that this is already done and it was not much of a help.

[it_support]

Hi All,

I have solved the issue. I know where to check the logs file and I do troubleshooting from there.
here are my code:
# Outbound Email Configuration#
mail.host= (your MX endpoint).protection.outlook.com
mail.port=25
mail.protocol=smtp
mail.username= (account name) #<— This is the email address used to log into Office 365
mail.smtps.starttls.enable=false
mail.smtps.auth=false
mail.from.default= (account name) #<—-(This has to be the same as the email use to log into Office365 in the mail.username config line)

I did setup SMTP relay connector in Office 365 portal (Login to Office 365 Portal > Exchange Admin Portal > Mail Flows > Connectors)
Hopefully it can help others who face the same issue like me.

Best regards,
Jumi