Could not connect to smtp.gmail.com:587

[kingiorikk]

Hello Sir:

I use mailsend program to send e-mail, but not work for smtp.gmail.com.

The following (1) and (2) are smtp server info when I send command via Show server info command.

When I send command to get yahoo mail server information that is work ok, but when I get gmail server information that is not work.

So How did I to solve this problem？ thanks

(1). //-----------gmail server info-----------// mailsend -v -info -port 587 -smtp smtp.gmail.com Connecting to SMTP server: smtp.gmail.com at Port: 587 Connection timeout: 5 secs libmsock: using getaddrinfo AF_INET6 IPv6 address: 2607:f8b0:400e:c03::6d EINPROGRESS=150,EWOULDBLOCK=11 connect(): socket=3,rc=-1, errno=128 AF_INET IPv4 IPv4 address: 74.125.129.108 EINPROGRESS=150,EWOULDBLOCK=11 connect(): socket=4,rc=-1, errno=124 AF_INET IPv4 IPv4 address: 74.125.129.109 EINPROGRESS=150,EWOULDBLOCK=11 connect(): socket=5,rc=-1, errno=124 Could not connect to smtp.gmail.com:587 Error: Could not connect to SMTP server "smtp.gmail.com" at port 587

(2). //-----------yahoo mail server info-----------// mailsend -v -info -port 587 -smtp smtp.mail.yahoo.com Connecting to SMTP server: smtp.mail.yahoo.com at Port: 587 Connection timeout: 5 secs libmsock: using getaddrinfo AF_INET IPv4 IPv4 address: 106.10.150.171 EINPROGRESS=150,EWOULDBLOCK=11 connect(): socket=3,rc=-1, errno=150 (Debug) Try socket 3 [S] 220 smtp.mail.yahoo.com ESMTP ready [C] EHLO localhost [S] 250-smtp.mail.yahoo.com [S] 250-PIPELINING [S] 250-SIZE 41697280 [S] 250-8 BITMIME [S] 250 STARTTLS [C] STARTTLS [S] 220 2.0.0 Start TLS Cipher: AES128-SHA Certificate information: Subject: /C=US/ST=CA/L=Sunnyvale/O=Yahoo! Inc./CN=smtp.mail.yahoo.com Issuer: /C=US/O=DigiCert Inc/OU=www.digicert.com/CN=DigiCert High Assurance CA-3 [C] EHLO localhost [S] 250-smtp.mail.yahoo.com [S] 250-PIPELINING [S] 250-SIZE 41697280 [S] 250-8 BITMIME [S] 250 AUTH PLAIN LOGIN XYMCOOKIE [C] QUIT [S] 221 2.0.0 Bye

[muquit]

Would you try the flag -4 to use the IPv4 address? You probably have IPv6 enabled in your machine but there is no IPv6 route.

[dreulavelle]

what is your from email? and the to email as well.. also when it comes to mailsend.exe, I'm not the biggest help considering that executable isn't mine ;) However I had to play around with the switches for my email to work. Although it should work for all gmail accounts.

[kingiorikk]

Dear muquit: You mean is don't use HAVE_GETADDRINFO. I try to don't use HAVE_GETADDRINFO, that is work ok.

[muquit]

did you try to run mailsend.exe with -4? By default mailsend will try to detect IPv4 or IPv6, if you have IPv6 stack enabled it will try to use it. However it may not work if you do not have a real IPv6 network. So if you use mailsend.exe -4 .... , it should work? Did you try that?

[kingiorikk]

Dear muquit: my test platform is mips platform, how did I try to run mailsend.exe with -4 on mips platform?

direct input command: mailsend -4 ?

[muquit]

You are running mailsend on that platform right? It's a command line option for mailsend to use IPv4 transport. Sorry I am confused what you are trying to do. The original issue was that mailsend can not connect to gmail at port 587 but it does connect to yahoo at that port. So I said to run mailsend with -4, like: mailsend -v -4 -info -port 587 -smtp smtp.gmail.com. Did it work or not? Note: -4 flag is available in mailsend v1.17b15+

[kingiorikk]

Dear muquit : Sorry late reply to you. I download mailsend version is mailsend-1.17b14. So cannot doing -4 command. However, I try to don't use HAVE_GETADDRINFO, that is work ok. So maybe the root cause is IPv6 enabled in my machine but there is no IPv6 route. I will try to test -4 command on mailsend v1.17b15+ later, and post my test report on here. Very thanks.

[jurraburu]

Hi Muquit,

I am trying to use mailsend (I´ve used it many years ago), but I allways receive Error: Could not connect to SMTP server ."66.96.163.138" at port 587

I tried with that server using the ip and the name, and also tried with mailsend -v -4 -info -port 587 -smtp smtp.gmail.com an with yahoo and our own server with the same results.

I am running on Windows 10

[jurraburu]

Sorry, was McAfee that was blocking mailsend.exe. It is solved!

[atesin]

don't use "EHLO localhost" or you could be blocked !!!

explanation: https://github.com/muquit/mailsend/issues/132#issuecomment-1637013321