Help Requested: Trying to rule out ISP Fuckery

Networking
21

Yeah, the old SSL SMTPS stuff is obsolete now and only used for legacy reasons. It's been replaced with STARTTLS. It should work on port 587 but you could also try port 25

22

Both 25 & 587 fail to send.

Edit: This is interesting. It's now telling me that the "connection was lost in the middle of the transaction." I have no idea what that means and am fairly sure I should have at least some idea.

23

Try port 465 with ssl/tls

24

smtp.gmail.com has the following ports open and not filtered:

25/tcp  open  smtp
465/tcp open  smtps
587/tcp open  submission
993/tcp open  imaps
995/tcp open  pop3s

It seems more likely you have to add your credentials to the outgoing connection settings in your mailclient.

25

Same error. You think this might have to do with the security method of "encrypted password"?

26

Yeah, this should probably be plain text password

27

Yes; I assume its actually pöain password over encrypted cannel. Turn off encrypted password as the transmission and the handshake at that time is already encrypted itselve.

28

OK, so setting it to 'password' (there's pw, encrypted pw, NTLM, & Kerberos GSSAPI btw) and trying ports 25, 465, & 587 I get a new error! This is getting a touch farcical.

"Sending of message failed.
The message could not be sent because the connection to SMTP server smtp.gmail.com timed out. Try again or contact your network administrator. Additionally, verify that your firewall or antivirus program is not preventing Postbox from sending email."

29

can you ping smtp.gmail.com? Do all the ports timeout?

30

All the ports give me that error, yes. And I can confirm that my firewall has been told to leave Postbox the hell alone, and that Avast should really have nothing to do with it besides quick checking.

31

I can indeed ping smtp.gmail.com, and I even get a great (for my ISP) response time. Average of 251ms.

32

When trying port 587 make sure to use STARTTLS and with port 465 try ssl/tls

1 Like
33

Yup, doublechecked those. No good.

34

Sorry that timeout after all leaves me scratching my head... Postbox does not eventually create logfiles? ((I assume we are on windows, are we?))

35

Windows7 Ultimate N, indeed. I should have specified that in the first place.

Well, I'm back after a(n amazing for once) sleep and a ridiculously busy day, though I have another similar tomorrow.

Let's see, log files. I don't think so. It does, however, create entries in the "error console." Anything I should be looking for in there?

36

Well the output of that said error console during the attemt to send an e-mail would be a start; maybe somone can read the error out of it ^^

37

I don't think it's useful. It doesn't even seem relevant. Not logfiles in general but the specific output of Postbox. Here, take a look.

38

Is it me, or is there nothing to look?

39

What?

40

Dont ask my why, but the image did not show, nore load nor waht ever for me before.. sry

And the output seems to have nothing to do with the client/server communication thats failing.
I am out of ideas for now to be honest =(