SSO Outlook 365 - email SSLHandshakeException

Send Email node error: PKIX Path building failed unable to find valid cer

I have successfully installed 2 .cer security certificates into KNIME AP (1 for the Office 365 web portal page, and 1 for the company website that is used for the email address domain) using the approach seen on Redit and here Resolving Common KNIME Certificates Problems - YouTube. The error persists. I have also adjusted the Office 365 setting for the email address to allow SMTP app connections. My node config settings match what was used in prior forum posts as well.

I also tried shifting the email address over to MFA with an App Password as was recommended in another post, however the App Password option doesn’t appear to be allowed without premium Azure AD licensing.

I am not finding much else out there on the web to troubleshoot at this point…

Hi iCFO,

Your setup does look right, so it’s likely that there is an email setting that needs to be set. Are POP/IMAP activated? Also, is 2-factor authentication set?


It must have been a combination of my Firewall and various outlook 365 server various admin settings, but it is working. It would certainly be nice if the send email node didn’t fail every time an empty field existed for an address controlled by a flow variable. Not every email in an email loop will necessarily have a CC, BCC or attachment…

Yes, it definitely shouldn’t be the case that the node fails on missing CC/BCC/attachments. If configuring the email nodes in a loop causes it to complain on missing values, I would add a case switch with flow variables and then set the cases where CC/BCC/attachments are empty. Will look into this though!


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It took an 8 way Case Switch to handle every possible missing field error point (and may require try catch on each stream) but it works.

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