• Unable to send email using the SendMessage service on a Thing with the MailServer Thing Template
• Unable to send email after upgrading to latest ThingWorx version.
• Mail server Thing is not working
• Unable to send messages via Alerts
• Cannot configure ThingWorx to send emails via Gmail server
• Having an issue with mail server configuration
• GMail account was updated for testing to Connect Less Secure Apps but connection still fails
• 504 Gateway Time out error in Mail server Thing: 

• Error message in Composer when testing service:

Unable to Invoke Service Service_Name on Thing_Name : Could not connect to SMTP host: smtp.gmail.com, port: 465

Unable to Invoke Service SendMessage on TW.RSM.SFW.Thing.MailServer : <ip address> SMTP; Client was not authenticated to send anonymous mail during MAIL FROM 

Unable to send error email for logged incident

• Errors appearing in \ThingworxStorage\logs\ApplicationLog.log:

[L: ERROR] [O: c.t.w.BaseService] [I: ] [U: <username>] [S: ] [T: http-nio-80-exec-8] [context: com.thingworx.webservices.context.HttpExecutionContext@4d87bcdb][message: Unable to Invoke Service SendMessage on <Thing> : null]

Wrapped com.sun.mail.smtp.SMTPSendFailedException: 550 5.7.60 SMTP; Client does not have permissions to send as this sender ###

Unable to Invoke Service SendMessage on <MailServerThing> : Unable to send error email for logged incident
 Transaction has been marked as a failure for request /Thingworx/Things/<MailServerThing>/Services/SendMessage

[L: ERROR] [O: E.c.q.l.c.Logger] [I: ] [U: Administrator] [S: ] [P: ] [T: https-openssl-nio-8443-exec-10] Error sending email due to  [535 5.7.3 Authentication unsuccessful_].The last server response was [535 5.7.3 Authentication unsuccessful_] with return code [535].The error originated on host [<hostname>]. 
[L: ERROR] [O: E.c.q.l.c.Logger] [I: ] [U: Administrator] [S: ] [P: ] [T: https-openssl-nio-8443-exec-10] Unable to send error email for logged incident: failed to connect, no password specified? 
[L: ERROR] [O: E.c.q.l.c.Logger] [I: ] [U: Administrator] [S: ] [P: ] [T: https-openssl-nio-8443-exec-10] Unable to Invoke Service SendMessage on MailTest : Unable to send error email for logged incident java.lang.Exception: Unable to send error email for logged incident

[L: ERROR] [O: E.c.q.l.c.Logger] [I: ] [U: Administrator] [S: ] [P: ] [T: https-jsse-nio-8443-exec-1] Error sending email due to [Couldn't connect to host, port: smtp, 25; timeout 30000].The last server response was [null] with return code [0].The error originated on host [HostName].

[L: ERROR] [O: E.c.q.l.c.Logger] [I: ] [U: Administrator] [S: ] [P: ] [T: https-jsse-nio-8443-exec-1] Unable to send error email for logged incident: Couldn't connect to host, port: smtp, 25; timeout 30000

[L: ERROR] [O: E.c.q.l.c.Logger] [I: ] [U: Administrator] [S: ] [P: ] [T: https-jsse-nio-8443-exec-1] Unable to Invoke Service SendMessage on MailServerThing : Unable to send error email for logged incident

[L: ERROR] [O: S.c.t.t.m.MailThing] [I: ] [U:] [S: ] [P: ] [T:http-nio-8080-exec-10] Authentication failed: Please make sure the credentials are correct.