If I uncheck the “Use SSL” box, then I get the error message of “530 Must issue a STARTTLS command first.” as would be expected.īetween that and packet inspecting, I can see that the STARTTLS is being sent and received by the server. I also had a volume with an older OSX on it (10.10.2), booted that up to test with a fresh install same response there. Manager on Windows handles whatever I throw at it. I’ve been having a play about with this all day, trying to hone in. On the Windows version, the error messages were more specific if incorrect data was entered, as opposed to only “Message could not be sent” on the Mac version. No difference.Īlso tested using Hotmail and Gmail SMTP (including allowing insecure logins for gmail), but still receive the same message.Įmails can be sent when not using a custom SMTP, or when using a custom SMTP that does not use SSL.Īlso tested Manager (16.3.24) on Windows and the custom SMTP works correctly as expected. No change.įrom address must match the account, have also tried with default no-reply. Use SSL is checked, have also tried without. “ ” 465 (SSL) / 587 (STARTTLS), with login required. Tested SMTP server in several email clients. Second Mac was a clean install with a business quickly created just to test SMTP connection. Both fail with the same message.įirst Mac was an existing business. Tested on two Macs both running El Capitan (10.11.13) using the latest Manager (16.3.24). I had previously been using an older version of Manager, and was unable to send emails using defaults or the custom SMTP and updated to the latest version as mentioned in the forums for the email issue.ĭoing so corrected the initial error message, though did not resolve the problem. Now I just need to figure out why I am not getting anything in the message part of the text.When trying to setup the custom SMTP server with the correct details, “Message could not be sent” error is shown when clicking to test email settings. It also seems very strange that one server can log into and send from different email domains. Why some smtp servers will work and why some others won't, I don't understand. Also tithe rochester.rr.com server the server.starttls() is not supported. If I use the server it doesn't matter what email account I try to log into I always get an authentication error. The script will complete with a account but no text is received.

If I use the rochester.rr.com server I can login and send email from a rochester.rr.com, and email account. If I use, 587 or 485,, 587 or, 587 the script will hang at the server=. I get this output only with .com, 587 or, 587. I am assuming that is some memory location since it changes each time I run the script. If I put a print(server) after server=smtplib.

Hotmail smtp not working mac