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tldr: I have a compiled AutoIt exe which uses Jos' _INetSmtpMailCom() UDF. It works as expected in 5 PCs with Windows 10 for about a year, now I set it up on a laptop with a fresh Install of Windows 10 and all the needed programs and it throws a com error 0x8002009 with description "The transport failed to connect to the server.". Everything works up until the point where the e-mail is to be sent ($objemail.Send ), with this I mean that the e-mail is composed correctly and saved in a file. The application reads a tab separated text file that is provided by the user, connects to a database to get additional info and composes a plain-text e-mail that is sent using _INetSmtpMailCom UDF. The _INetSmtpMailCom is slightly modified to support STARTTLS as it's used with a microsoft account. I just added this line: $objEmail.Configuration.Fields.Item ("http://schemas.microsoft.com/cdo/configuration/sendtls") = True In this post for the same error number it was suggested to check the TLS version supported in internet properties, in my case this was correct. I found that com error 0x8002009 is just a generic error in windows: DISP_E_EXCEPTION - "Exception occurred". Overall, every solution I found either addresses a server-side problem, is specific to a different language e.g. "include typelib in VBS" or addresses problems in a code that is not working. Also, most of them are at least eight years old. I didn't include any code in the post as I think that the problem is in the configuration of the laptop, not in my code, because it is used everyday for about a year and it works as expected on the other PCs. Did something like this happened to you? Do you have any ideas what else should I check? Some history: The error 0x8002009 "The transport failed to connect to the server." is the second error in line, I ended up here after fixing the previous error 0x8002009 "The requested body part was not found in this message." that was due to the region language being "English (Europe)", a format that older windows editions didn't have so CDO.Message didn't take it very well. Now the laptop has the same region language as the other 5 PCs.