Email Tool - SMTP Settings, SSL Connection Error

[andrew2786]

Hi everyone,

I'm trying to configure the Email tool and get the following error: 'SSL Connection Error - Check the SMTP server address and port number'

We use Office 365 and I've been given the following details by our IT dept:

Server/smart host: smtp.office365.com
Port: Port 587 (recommended) or port 25
TLS/StartTLS     SSL/TSL

Configuring the tool as follows (obviously using a proper username and password):

I've also tried port 25, with no luck.

Any ideas what might be going wrong?

Thanks

[mceleavey]

Hi @andrew2786 ,

this could be a couple of things. First, try using the STARTTLS rather than SSL authentication.

Second, check with your IT team that the ports you are trying are the ports they are using for SMTP and that the ports have been forwarded.

M.

[andrew2786]

Hi @mceleavey,

STARTTLS didn't work ('Login denied') - have tried different port options.

IT have said that 587 and 25 are the usual ports used by Office 365 for sending emails via SMTP.

What might be next to try?

Thanks

[mceleavey]

@andrew2786 ,

and you're using your email address and password for Office 365, or a designated account?

I use the email tool with Office 365 frequently, and this is the configuration that works for me:

[andrew2786]

Thanks, but unfortunately that doesn't work for us.

With that configuration using STARTTLS I get a 'Record#1: Login denied' error.

The username and password are the same ones I use to login to Office locally, and have checked they work when logging into Office online via their website

[kc03]

Hi @andrew2786 and @mceleavey 

Lately I have also started getting sporadic errors both on the server and on my local machine.

Strange point is that I am not getting this for all records but just 1. And if I run the same workflow again, it works fine. 

PROD Send EMail v2 (85) Record #31: Tool #33: Record#1: SSL Connection Error - Check the SMTP server address and port number

Any suggestions?

[andrew2786]

I don't know why you'd be getting an error for just 1 record kc03, sorry.

We now believe that our error messages are related to the fact we have multi-factor authentication on our O365 accounts i.e. Alteryx's username/password authentication in the email tool doesn't go far enough to authenticate.

Has anyone else run into this before and is there a workaround? 

[kc03]

@andrew2786 were you able to solve this issue or you still getting this error?

I found out that there are other people in my firm who are getting this error sporadically. But not sure about the root cause. I don't see anyone has reported this issue on the Alteryx community before. 

[Tmanuela]

@kc03 I am facing the same trouble sporadic with this error where nothing was changed at the workflow that worked fine.

[VeenaHiremath21]

Hi Team ,

Even I am facing same issue

Can any one please help me on this