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muquit / mailsend

A program to send mail via SMTP from command line
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mailsend not working with smtp.live.com #100

Open SirDan1963 opened 7 years ago

SirDan1963 commented 7 years ago

Hello,

Love your program. I am using mailsend v1.19 compiled with OpenSSL. Sending email through my Gmail account works if I turn on allow access for less secure apps. Without that setting turned on, sending to Gmail fails with Authentication Failed error.

I am needing to use smtp.live.com also for sending. I am having the same problem Authentication Failed, but I cannot find any setting to allow less secure apps.

Why does sending to Gmail fail unless allow less secure apps is turned on? Why does sending to smtp.live.com fail with Authentication Failed? Is there a setting for smtp.live.com to allow less secure apps? Is there a fix available for mailsend please?

Below is what I send, and the reply. Thank you,

` [root@RMS-200 /root]# mailsend -to me@you.net -from RMS300@xxxxxxxx.xx -starttls -port 587 -auth -smtp smtp.live.com -sub test -v -user xxxxxxxxx@hotmail.com -pass "xxxxxxxxxxxxxxx" Connecting to smtp.live.com:587 Will detect IPv4 or IPv6 automatically

libmsock: using getaddrinfo AF_INET IPv4 IPv4 address: 65.55.176.126 EINPROGRESS=115,EWOULDBLOCK=11 connect(): socket=3,rc=-1, errno=115 Try socket 3 Setting read timeout to: 5 seconds [S] 220 BLU436-SMTP156.smtp.hotmail.com Microsoft ESMTP MAIL Service, Version: 8.0.9200.16384 ready at Sun, 11 Sep 2016 11:54:10 -0700 [C] EHLO localhost Setting read timeout to: 5 seconds [S] 250-BLU436-SMTP156.smtp.hotmail.com Hello [xxx.xxx.xxx.xxx] Setting read timeout to: 5 seconds [S] 250-TURN Setting read timeout to: 5 seconds [S] 250-SIZE 41943040 Setting read timeout to: 5 seconds [S] 250-ETRN Setting read timeout to: 5 seconds [S] 250-PIPELINING Setting read timeout to: 5 seconds [S] 250-DSN Setting read timeout to: 5 seconds [S] 250-ENHANCEDSTATUSCODES Setting read timeout to: 5 seconds [S] 250-8bitmime Setting read timeout to: 5 seconds [S] 250-BINARYMIME Setting read timeout to: 5 seconds [S] 250-CHUNKING Setting read timeout to: 5 seconds [S] 250-VRFY Setting read timeout to: 5 seconds [S] 250-TLS Setting read timeout to: 5 seconds [S] 250-STARTTLS Setting read timeout to: 5 seconds [S] 250 OK [C] STARTTLS Setting read timeout to: 5 seconds [S] 220 2.0.0 SMTP server ready Cipher: AES256-SHA Certificate information: Subject: /C=US/ST=Washington/L=Redmond/O=Microsoft Corporation/CN=*.hotmail.com Issuer: /C=BE/O=GlobalSign nv-sa/CN=GlobalSign Organization Validation CA - SHA256 - G2 [C] EHLO localhost [S] 250-BLU436-SMTP156.smtp.hotmail.com Hello [xxx.xxx.xxx.xxx] [S] 250-TURN [S] 250-SIZE 41943040 [S] 250-ETRN [S] 250-PIPELINING [S] 250-DSN [S] 250-ENHANCEDSTATUSCODES [S] 250-8bitmime [S] 250-BINARYMIME [S] 250-CHUNKING [S] 250-VRFY [S] 250-AUTH LOGIN PLAIN XOAUTH2 [S] 250 OK Server does not support AUTH CRAM-MD5 Using AUTH LOGIN [C] AUTH LOGIN [S] 334 xxxxxxxxxxxxx [C] xxxxxxxxxxxxxxxxxxxxxxxxx [S] 334 xxxxxxxxxxxxx [C] xxxxxxxxxxxxxxxxxxxxxxxxx [S] 535 5.0.0 Authentication Failed Error: AUTH LOGIN failed: '535 5.0.0 Authentication Failed' Could not send mail`

muquit commented 7 years ago

Google considers all apps insecure other than their own. For gmail, you can turn on 2F authentication and then generate an app specific password to use mailsend as a secure app. For smtp.live.com, did you try PLAIN mechanism? Also in Windows if your password contains 8 bit characters, it won't work. It is a known limitation of mailsend in windows. Thanks

muquit commented 7 years ago

I just tested smtp.live.com. It worked fine with LOGIN mechanism. I used mailsend v1.19 on Mac however. I will test it from Windows tomorrow. Thanks

SirDan1963 commented 7 years ago

Hello,

Thank you for the super fast response. My test machine is Linux. I did try -auth-plain, same result. I must be doing something wrong, I will keep playing with it.

AndrewZim commented 7 years ago

I found I need to use -ehlo with office365.

SirDan1963 commented 7 years ago

Hello,

Thank you for the info. I tried the -ehlo with hotmail.com but still cannot make it work. I have mailsend compiled with OpenSSL 0.9.8k. Could that be the problem, maybe too old?

The password has lots of weird characters like &$#! etc, could that be an issue?

For a work around, I have mailsend sending to a gmail account which forwards to a microsoft exchange email server

Connecting to smtp.live.com:587 Will detect IPv4 or IPv6 automatically

libmsock: using getaddrinfo AF_INET IPv4 IPv4 address: 65.55.163.152 EINPROGRESS=115,EWOULDBLOCK=11 connect(): socket=3,rc=-1, errno=115 Try socket 3 Setting read timeout to: 5 seconds [S] 220 BLU437-SMTP32.smtp.hotmail.com Microsoft ESMTP MAIL Service, Version: 8.0.9200.16384 ready at Tue, 11 Oct 2016 18:01:34 -0700 [C] EHLO localhost Setting read timeout to: 5 seconds [S] 250-BLU437-SMTP32.smtp.hotmail.com Hello [XXXXXXXXXXXXXXXXX] Setting read timeout to: 5 seconds [S] 250-TURN Setting read timeout to: 5 seconds [S] 250-SIZE 41943040 Setting read timeout to: 5 seconds [S] 250-ETRN Setting read timeout to: 5 seconds [S] 250-PIPELINING Setting read timeout to: 5 seconds [S] 250-DSN Setting read timeout to: 5 seconds [S] 250-ENHANCEDSTATUSCODES Setting read timeout to: 5 seconds [S] 250-8bitmime Setting read timeout to: 5 seconds [S] 250-BINARYMIME Setting read timeout to: 5 seconds [S] 250-CHUNKING Setting read timeout to: 5 seconds [S] 250-VRFY Setting read timeout to: 5 seconds [S] 250-TLS Setting read timeout to: 5 seconds [S] 250-STARTTLS Setting read timeout to: 5 seconds [S] 250 OK [C] STARTTLS Setting read timeout to: 5 seconds [S] 220 2.0.0 SMTP server ready Cipher: AES256-SHA Certificate information: Subject: /C=US/ST=Washington/L=Redmond/O=Microsoft Corporation/CN=*.hotmail.com Issuer: /C=BE/O=GlobalSign nv-sa/CN=GlobalSign Organization Validation CA - SHA256 - G2 [C] EHLO localhost [S] 250-BLU437-SMTP32.smtp.hotmail.com Hello [XXXXXXXXXXXXXX] [S] 250-TURN [S] 250-SIZE 41943040 [S] 250-ETRN [S] 250-PIPELINING [S] 250-DSN [S] 250-ENHANCEDSTATUSCODES [S] 250-8bitmime [S] 250-BINARYMIME [S] 250-CHUNKING [S] 250-VRFY [S] 250-AUTH LOGIN PLAIN XOAUTH2 [S] 250 OK Using AUTH LOGIN [C] AUTH LOGIN [S] 334 XXXXXXXXXXXXXXXXXX [C] XXXXXXXXXXXXXXXXXXXXXX [S] 334 XXXXXXXXXXXXXXXXXX [C] XXXXXXXXXXXXXXXXXXXXXX [S] 535 5.0.0 Authentication Failed Error: AUTH LOGIN failed: '535 5.0.0 Authentication Failed' Could not send mail

Dan Pattison

On 10/11/2016 5:21 PM, AndrewZim wrote:

I found I need to use -ehlo with office365.

— You are receiving this because you authored the thread. Reply to this email directly, view it on GitHub https://github.com/muquit/mailsend/issues/100#issuecomment-253084844, or mute the thread https://github.com/notifications/unsubscribe-auth/AHk-h_7THbqDI0ANqH6eS_jiwutV80khks5qzCgigaJpZM4J6Fgf.

AndrewZim commented 7 years ago

Can you provide your command line syntax? I use -ehlo -auth -starttls with smtp.office365.com.

Andrew Zimmerman ABC Softek LLC andrew@abcsoftek.commailto:andrew@abcsoftek.com www.SimplifyMyBiz.comhttp://www.simplifymybiz.com/

From: SirDan1963 [mailto:notifications@github.com] Sent: Tuesday, October 11, 2016 9:15 PM To: muquit/mailsend mailsend@noreply.github.com Cc: Andrew Zimmerman andrew@abcsoftek.com; Comment comment@noreply.github.com Subject: Re: [muquit/mailsend] mailsend not working with smtp.live.com (#100)

Hello,

Thank you for the info. I tried the -ehlo with hotmail.com but still cannot make it work. I have mailsend compiled with OpenSSL 0.9.8k. Could that be the problem, maybe too old?

The password has lots of weird characters like &$#! etc, could that be an issue?

For a work around, I have mailsend sending to a gmail account which forwards to a microsoft exchange email server

Connecting to smtp.live.com:587 Will detect IPv4 or IPv6 automatically

libmsock: using getaddrinfo AF_INET IPv4 IPv4 address: 65.55.163.152 EINPROGRESS=115,EWOULDBLOCK=11 connect(): socket=3,rc=-1, errno=115 Try socket 3 Setting read timeout to: 5 seconds [S] 220 BLU437-SMTP32.smtp.hotmail.com Microsoft ESMTP MAIL Service, Version: 8.0.9200.16384 ready at Tue, 11 Oct 2016 18:01:34 -0700 [C] EHLO localhost Setting read timeout to: 5 seconds [S] 250-BLU437-SMTP32.smtp.hotmail.com Hello [XXXXXXXXXXXXXXXXX] Setting read timeout to: 5 seconds [S] 250-TURN Setting read timeout to: 5 seconds [S] 250-SIZE 41943040 Setting read timeout to: 5 seconds [S] 250-ETRN Setting read timeout to: 5 seconds [S] 250-PIPELINING Setting read timeout to: 5 seconds [S] 250-DSN Setting read timeout to: 5 seconds [S] 250-ENHANCEDSTATUSCODES Setting read timeout to: 5 seconds [S] 250-8bitmime Setting read timeout to: 5 seconds [S] 250-BINARYMIME Setting read timeout to: 5 seconds [S] 250-CHUNKING Setting read timeout to: 5 seconds [S] 250-VRFY Setting read timeout to: 5 seconds [S] 250-TLS Setting read timeout to: 5 seconds [S] 250-STARTTLS Setting read timeout to: 5 seconds [S] 250 OK [C] STARTTLS Setting read timeout to: 5 seconds [S] 220 2.0.0 SMTP server ready Cipher: AES256-SHA Certificate information: Subject: /C=US/ST=Washington/L=Redmond/O=Microsoft Corporation/CN=*.hotmail.com Issuer: /C=BE/O=GlobalSign nv-sa/CN=GlobalSign Organization Validation CA - SHA256 - G2 [C] EHLO localhost [S] 250-BLU437-SMTP32.smtp.hotmail.com Hello [XXXXXXXXXXXXXX] [S] 250-TURN [S] 250-SIZE 41943040 [S] 250-ETRN [S] 250-PIPELINING [S] 250-DSN [S] 250-ENHANCEDSTATUSCODES [S] 250-8bitmime [S] 250-BINARYMIME [S] 250-CHUNKING [S] 250-VRFY [S] 250-AUTH LOGIN PLAIN XOAUTH2 [S] 250 OK Using AUTH LOGIN [C] AUTH LOGIN [S] 334 XXXXXXXXXXXXXXXXXX [C] XXXXXXXXXXXXXXXXXXXXXX [S] 334 XXXXXXXXXXXXXXXXXX [C] XXXXXXXXXXXXXXXXXXXXXX [S] 535 5.0.0 Authentication Failed Error: AUTH LOGIN failed: '535 5.0.0 Authentication Failed' Could not send mail

Dan Pattison

On 10/11/2016 5:21 PM, AndrewZim wrote:

I found I need to use -ehlo with office365.

— You are receiving this because you authored the thread. Reply to this email directly, view it on GitHub https://github.com/muquit/mailsend/issues/100#issuecomment-253084844, or mute the thread https://github.com/notifications/unsubscribe-auth/AHk-h_7THbqDI0ANqH6eS_jiwutV80khks5qzCgigaJpZM4J6Fgf.

— You are receiving this because you commented. Reply to this email directly, view it on GitHubhttps://github.com/muquit/mailsend/issues/100#issuecomment-253092075, or mute the threadhttps://github.com/notifications/unsubscribe-auth/AHKsO9nltQDcgdbN9NoRD4XNmMQ4IMbxks5qzDR8gaJpZM4J6Fgf.

SirDan1963 commented 7 years ago

Hello Andrew,

The command line syntax below.

mailsend -to some@hotmailaddress.com -from RMS300@somewhere.ca -starttls -port 587 -auth -smtp smtp.live.com -sub test -v -user myhotmailaccount@hotmail.com -pass "#################" -ehlo

Thank you,

Dan Pattison EtherTek Circuits

On 10/12/2016 5:06 AM, AndrewZim wrote:

Can you provide your command line syntax? I use -ehlo -auth -starttls with smtp.office365.com.

Andrew Zimmerman ABC Softek LLC andrew@abcsoftek.commailto:andrew@abcsoftek.com www.SimplifyMyBiz.comhttp://www.simplifymybiz.com/

From: SirDan1963 [mailto:notifications@github.com] Sent: Tuesday, October 11, 2016 9:15 PM To: muquit/mailsend mailsend@noreply.github.com Cc: Andrew Zimmerman andrew@abcsoftek.com; Comment comment@noreply.github.com Subject: Re: [muquit/mailsend] mailsend not working with smtp.live.com (#100)

Hello,

Thank you for the info. I tried the -ehlo with hotmail.com but still cannot make it work. I have mailsend compiled with OpenSSL 0.9.8k. Could that be the problem, maybe too old?

The password has lots of weird characters like &$#! etc, could that be an issue?

For a work around, I have mailsend sending to a gmail account which forwards to a microsoft exchange email server

Connecting to smtp.live.com:587 Will detect IPv4 or IPv6 automatically

libmsock: using getaddrinfo AF_INET IPv4 IPv4 address: 65.55.163.152 EINPROGRESS=115,EWOULDBLOCK=11 connect(): socket=3,rc=-1, errno=115 Try socket 3 Setting read timeout to: 5 seconds [S] 220 BLU437-SMTP32.smtp.hotmail.com Microsoft ESMTP MAIL Service, Version: 8.0.9200.16384 ready at Tue, 11 Oct 2016 18:01:34 -0700 [C] EHLO localhost Setting read timeout to: 5 seconds [S] 250-BLU437-SMTP32.smtp.hotmail.com Hello [XXXXXXXXXXXXXXXXX] Setting read timeout to: 5 seconds [S] 250-TURN Setting read timeout to: 5 seconds [S] 250-SIZE 41943040 Setting read timeout to: 5 seconds [S] 250-ETRN Setting read timeout to: 5 seconds [S] 250-PIPELINING Setting read timeout to: 5 seconds [S] 250-DSN Setting read timeout to: 5 seconds [S] 250-ENHANCEDSTATUSCODES Setting read timeout to: 5 seconds [S] 250-8bitmime Setting read timeout to: 5 seconds [S] 250-BINARYMIME Setting read timeout to: 5 seconds [S] 250-CHUNKING Setting read timeout to: 5 seconds [S] 250-VRFY Setting read timeout to: 5 seconds [S] 250-TLS Setting read timeout to: 5 seconds [S] 250-STARTTLS Setting read timeout to: 5 seconds [S] 250 OK [C] STARTTLS Setting read timeout to: 5 seconds [S] 220 2.0.0 SMTP server ready Cipher: AES256-SHA Certificate information: Subject: /C=US/ST=Washington/L=Redmond/O=Microsoft Corporation/CN=*.hotmail.com Issuer: /C=BE/O=GlobalSign nv-sa/CN=GlobalSign Organization Validation CA - SHA256 - G2 [C] EHLO localhost [S] 250-BLU437-SMTP32.smtp.hotmail.com Hello [XXXXXXXXXXXXXX] [S] 250-TURN [S] 250-SIZE 41943040 [S] 250-ETRN [S] 250-PIPELINING [S] 250-DSN [S] 250-ENHANCEDSTATUSCODES [S] 250-8bitmime [S] 250-BINARYMIME [S] 250-CHUNKING [S] 250-VRFY [S] 250-AUTH LOGIN PLAIN XOAUTH2 [S] 250 OK Using AUTH LOGIN [C] AUTH LOGIN [S] 334 XXXXXXXXXXXXXXXXXX [C] XXXXXXXXXXXXXXXXXXXXXX [S] 334 XXXXXXXXXXXXXXXXXX [C] XXXXXXXXXXXXXXXXXXXXXX [S] 535 5.0.0 Authentication Failed Error: AUTH LOGIN failed: '535 5.0.0 Authentication Failed' Could not send mail

Dan Pattison

On 10/11/2016 5:21 PM, AndrewZim wrote:

I found I need to use -ehlo with office365.

— You are receiving this because you authored the thread. Reply to this email directly, view it on GitHub https://github.com/muquit/mailsend/issues/100#issuecomment-253084844, or mute the thread

https://github.com/notifications/unsubscribe-auth/AHk-h_7THbqDI0ANqH6eS_jiwutV80khks5qzCgigaJpZM4J6Fgf.

— You are receiving this because you commented. Reply to this email directly, view it on GitHubhttps://github.com/muquit/mailsend/issues/100#issuecomment-253092075, or mute the threadhttps://github.com/notifications/unsubscribe-auth/AHKsO9nltQDcgdbN9NoRD4XNmMQ4IMbxks5qzDR8gaJpZM4J6Fgf.

— You are receiving this because you authored the thread. Reply to this email directly, view it on GitHub https://github.com/muquit/mailsend/issues/100#issuecomment-253195563, or mute the thread https://github.com/notifications/unsubscribe-auth/AHk-hzqY09LfBwxP0jjYjVjHUSuUnVDTks5qzM1HgaJpZM4J6Fgf.

AndrewZim commented 7 years ago

You might try -auth-login and -auth-plain instead of -auth, which tries several different types, and may be aborting.

I’ve had to increase timeouts with ‘-ct 90 -read-timeout 90’ on some servers.

It may be a problem with password characters not being transmitted correctly. Try to simplify the password.

I’m interested in any results, as we’re using mailsend with various custom applications. I have a page here to track notes on different servers: http://www.abcsoftware.us/wiki/configure-one-click-email/

Andrew Zimmerman ABC Softek LLC andrew@abcsoftek.commailto:andrew@abcsoftek.com www.SimplifyMyBiz.comhttp://www.simplifymybiz.com/

From: SirDan1963 [mailto:notifications@github.com] Sent: Wednesday, October 12, 2016 9:53 AM To: muquit/mailsend mailsend@noreply.github.com Cc: Andrew Zimmerman andrew@abcsoftek.com; Comment comment@noreply.github.com Subject: Re: [muquit/mailsend] mailsend not working with smtp.live.com (#100)

Hello Andrew,

The command line syntax below.

mailsend -to some@hotmailaddress.com -from RMS300@somewhere.ca -starttls -port 587 -auth -smtp smtp.live.com -sub test -v -user myhotmailaccount@hotmail.com -pass "#################" -ehlo

Thank you,

Dan Pattison EtherTek Circuits

On 10/12/2016 5:06 AM, AndrewZim wrote:

Can you provide your command line syntax? I use -ehlo -auth -starttls with smtp.office365.com.

Andrew Zimmerman ABC Softek LLC andrew@abcsoftek.commailto:andrew@abcsoftek.com www.SimplifyMyBiz.comhttp://www.simplifymybiz.com/

From: SirDan1963 [mailto:notifications@github.com] Sent: Tuesday, October 11, 2016 9:15 PM To: muquit/mailsend mailsend@noreply.github.com Cc: Andrew Zimmerman andrew@abcsoftek.com; Comment comment@noreply.github.com Subject: Re: [muquit/mailsend] mailsend not working with smtp.live.com (#100)

Hello,

Thank you for the info. I tried the -ehlo with hotmail.com but still cannot make it work. I have mailsend compiled with OpenSSL 0.9.8k. Could that be the problem, maybe too old?

The password has lots of weird characters like &$#! etc, could that be an issue?

For a work around, I have mailsend sending to a gmail account which forwards to a microsoft exchange email server

Connecting to smtp.live.com:587 Will detect IPv4 or IPv6 automatically

libmsock: using getaddrinfo AF_INET IPv4 IPv4 address: 65.55.163.152 EINPROGRESS=115,EWOULDBLOCK=11 connect(): socket=3,rc=-1, errno=115 Try socket 3 Setting read timeout to: 5 seconds [S] 220 BLU437-SMTP32.smtp.hotmail.com Microsoft ESMTP MAIL Service, Version: 8.0.9200.16384 ready at Tue, 11 Oct 2016 18:01:34 -0700 [C] EHLO localhost Setting read timeout to: 5 seconds [S] 250-BLU437-SMTP32.smtp.hotmail.com Hello [XXXXXXXXXXXXXXXXX] Setting read timeout to: 5 seconds [S] 250-TURN Setting read timeout to: 5 seconds [S] 250-SIZE 41943040 Setting read timeout to: 5 seconds [S] 250-ETRN Setting read timeout to: 5 seconds [S] 250-PIPELINING Setting read timeout to: 5 seconds [S] 250-DSN Setting read timeout to: 5 seconds [S] 250-ENHANCEDSTATUSCODES Setting read timeout to: 5 seconds [S] 250-8bitmime Setting read timeout to: 5 seconds [S] 250-BINARYMIME Setting read timeout to: 5 seconds [S] 250-CHUNKING Setting read timeout to: 5 seconds [S] 250-VRFY Setting read timeout to: 5 seconds [S] 250-TLS Setting read timeout to: 5 seconds [S] 250-STARTTLS Setting read timeout to: 5 seconds [S] 250 OK [C] STARTTLS Setting read timeout to: 5 seconds [S] 220 2.0.0 SMTP server ready Cipher: AES256-SHA Certificate information: Subject: /C=US/ST=Washington/L=Redmond/O=Microsoft Corporation/CN=*.hotmail.com Issuer: /C=BE/O=GlobalSign nv-sa/CN=GlobalSign Organization Validation CA - SHA256 - G2 [C] EHLO localhost [S] 250-BLU437-SMTP32.smtp.hotmail.com Hello [XXXXXXXXXXXXXX] [S] 250-TURN [S] 250-SIZE 41943040 [S] 250-ETRN [S] 250-PIPELINING [S] 250-DSN [S] 250-ENHANCEDSTATUSCODES [S] 250-8bitmime [S] 250-BINARYMIME [S] 250-CHUNKING [S] 250-VRFY [S] 250-AUTH LOGIN PLAIN XOAUTH2 [S] 250 OK Using AUTH LOGIN [C] AUTH LOGIN [S] 334 XXXXXXXXXXXXXXXXXX [C] XXXXXXXXXXXXXXXXXXXXXX [S] 334 XXXXXXXXXXXXXXXXXX [C] XXXXXXXXXXXXXXXXXXXXXX [S] 535 5.0.0 Authentication Failed Error: AUTH LOGIN failed: '535 5.0.0 Authentication Failed' Could not send mail

Dan Pattison

On 10/11/2016 5:21 PM, AndrewZim wrote:

I found I need to use -ehlo with office365.

— You are receiving this because you authored the thread. Reply to this email directly, view it on GitHub https://github.com/muquit/mailsend/issues/100#issuecomment-253084844, or mute the thread

https://github.com/notifications/unsubscribe-auth/AHk-h_7THbqDI0ANqH6eS_jiwutV80khks5qzCgigaJpZM4J6Fgf.

— You are receiving this because you commented. Reply to this email directly, view it on GitHubhttps://github.com/muquit/mailsend/issues/100#issuecomment-253092075, or mute the threadhttps://github.com/notifications/unsubscribe-auth/AHKsO9nltQDcgdbN9NoRD4XNmMQ4IMbxks5qzDR8gaJpZM4J6Fgf.

— You are receiving this because you authored the thread. Reply to this email directly, view it on GitHub https://github.com/muquit/mailsend/issues/100#issuecomment-253195563, or mute the thread https://github.com/notifications/unsubscribe-auth/AHk-hzqY09LfBwxP0jjYjVjHUSuUnVDTks5qzM1HgaJpZM4J6Fgf.

— You are receiving this because you commented. Reply to this email directly, view it on GitHubhttps://github.com/muquit/mailsend/issues/100#issuecomment-253219563, or mute the threadhttps://github.com/notifications/unsubscribe-auth/AHKsO8H5Aenp3BUHWJ1Z0ittGx_aqBqBks5qzOZJgaJpZM4J6Fgf.

AndrewZim commented 7 years ago

By the way, your command line works fine with my Office365 service.

Andrew Zimmerman ABC Softek LLC andrew@abcsoftek.commailto:andrew@abcsoftek.com www.SimplifyMyBiz.comhttp://www.simplifymybiz.com/

From: SirDan1963 [mailto:notifications@github.com] Sent: Wednesday, October 12, 2016 9:53 AM To: muquit/mailsend mailsend@noreply.github.com Cc: Andrew Zimmerman andrew@abcsoftek.com; Comment comment@noreply.github.com Subject: Re: [muquit/mailsend] mailsend not working with smtp.live.com (#100)

Hello Andrew,

The command line syntax below.

mailsend -to some@hotmailaddress.com -from RMS300@somewhere.ca -starttls -port 587 -auth -smtp smtp.live.com -sub test -v -user myhotmailaccount@hotmail.com -pass "#################" -ehlo

Thank you,

Dan Pattison EtherTek Circuits

On 10/12/2016 5:06 AM, AndrewZim wrote:

Can you provide your command line syntax? I use -ehlo -auth -starttls with smtp.office365.com.

Andrew Zimmerman ABC Softek LLC andrew@abcsoftek.commailto:andrew@abcsoftek.com www.SimplifyMyBiz.comhttp://www.simplifymybiz.com/

From: SirDan1963 [mailto:notifications@github.com] Sent: Tuesday, October 11, 2016 9:15 PM To: muquit/mailsend mailsend@noreply.github.com Cc: Andrew Zimmerman andrew@abcsoftek.com; Comment comment@noreply.github.com Subject: Re: [muquit/mailsend] mailsend not working with smtp.live.com (#100)

Hello,

Thank you for the info. I tried the -ehlo with hotmail.com but still cannot make it work. I have mailsend compiled with OpenSSL 0.9.8k. Could that be the problem, maybe too old?

The password has lots of weird characters like &$#! etc, could that be an issue?

For a work around, I have mailsend sending to a gmail account which forwards to a microsoft exchange email server

Connecting to smtp.live.com:587 Will detect IPv4 or IPv6 automatically

libmsock: using getaddrinfo AF_INET IPv4 IPv4 address: 65.55.163.152 EINPROGRESS=115,EWOULDBLOCK=11 connect(): socket=3,rc=-1, errno=115 Try socket 3 Setting read timeout to: 5 seconds [S] 220 BLU437-SMTP32.smtp.hotmail.com Microsoft ESMTP MAIL Service, Version: 8.0.9200.16384 ready at Tue, 11 Oct 2016 18:01:34 -0700 [C] EHLO localhost Setting read timeout to: 5 seconds [S] 250-BLU437-SMTP32.smtp.hotmail.com Hello [XXXXXXXXXXXXXXXXX] Setting read timeout to: 5 seconds [S] 250-TURN Setting read timeout to: 5 seconds [S] 250-SIZE 41943040 Setting read timeout to: 5 seconds [S] 250-ETRN Setting read timeout to: 5 seconds [S] 250-PIPELINING Setting read timeout to: 5 seconds [S] 250-DSN Setting read timeout to: 5 seconds [S] 250-ENHANCEDSTATUSCODES Setting read timeout to: 5 seconds [S] 250-8bitmime Setting read timeout to: 5 seconds [S] 250-BINARYMIME Setting read timeout to: 5 seconds [S] 250-CHUNKING Setting read timeout to: 5 seconds [S] 250-VRFY Setting read timeout to: 5 seconds [S] 250-TLS Setting read timeout to: 5 seconds [S] 250-STARTTLS Setting read timeout to: 5 seconds [S] 250 OK [C] STARTTLS Setting read timeout to: 5 seconds [S] 220 2.0.0 SMTP server ready Cipher: AES256-SHA Certificate information: Subject: /C=US/ST=Washington/L=Redmond/O=Microsoft Corporation/CN=*.hotmail.com Issuer: /C=BE/O=GlobalSign nv-sa/CN=GlobalSign Organization Validation CA - SHA256 - G2 [C] EHLO localhost [S] 250-BLU437-SMTP32.smtp.hotmail.com Hello [XXXXXXXXXXXXXX] [S] 250-TURN [S] 250-SIZE 41943040 [S] 250-ETRN [S] 250-PIPELINING [S] 250-DSN [S] 250-ENHANCEDSTATUSCODES [S] 250-8bitmime [S] 250-BINARYMIME [S] 250-CHUNKING [S] 250-VRFY [S] 250-AUTH LOGIN PLAIN XOAUTH2 [S] 250 OK Using AUTH LOGIN [C] AUTH LOGIN [S] 334 XXXXXXXXXXXXXXXXXX [C] XXXXXXXXXXXXXXXXXXXXXX [S] 334 XXXXXXXXXXXXXXXXXX [C] XXXXXXXXXXXXXXXXXXXXXX [S] 535 5.0.0 Authentication Failed Error: AUTH LOGIN failed: '535 5.0.0 Authentication Failed' Could not send mail

Dan Pattison

On 10/11/2016 5:21 PM, AndrewZim wrote:

I found I need to use -ehlo with office365.

— You are receiving this because you authored the thread. Reply to this email directly, view it on GitHub https://github.com/muquit/mailsend/issues/100#issuecomment-253084844, or mute the thread

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SirDan1963 commented 7 years ago

Hi Andrew,

I tried all of your suggestions, still no go. It must be something on my end, but I have no idea what. The only thing I keep coming back to is my older version of openssl. For now my work around of sending to a gmail account and having it forward to an MS exchange server is a working cludge. Thanks for all your suggestions.

Regards,

Dan Pattison EtherTek Circuits

On 10/12/2016 7:09 AM, AndrewZim wrote:

By the way, your command line works fine with my Office365 service.

Andrew Zimmerman ABC Softek LLC andrew@abcsoftek.commailto:andrew@abcsoftek.com www.SimplifyMyBiz.comhttp://www.simplifymybiz.com/

From: SirDan1963 [mailto:notifications@github.com] Sent: Wednesday, October 12, 2016 9:53 AM To: muquit/mailsend mailsend@noreply.github.com Cc: Andrew Zimmerman andrew@abcsoftek.com; Comment comment@noreply.github.com Subject: Re: [muquit/mailsend] mailsend not working with smtp.live.com (#100)

Hello Andrew,

The command line syntax below.

mailsend -to some@hotmailaddress.com -from RMS300@somewhere.ca -starttls -port 587 -auth -smtp smtp.live.com -sub test -v -user myhotmailaccount@hotmail.com -pass "#################" -ehlo

Thank you,

Dan Pattison EtherTek Circuits

On 10/12/2016 5:06 AM, AndrewZim wrote:

Can you provide your command line syntax? I use -ehlo -auth -starttls with smtp.office365.com.

Andrew Zimmerman ABC Softek LLC andrew@abcsoftek.commailto:andrew@abcsoftek.com www.SimplifyMyBiz.comhttp://www.simplifymybiz.com/

From: SirDan1963 [mailto:notifications@github.com] Sent: Tuesday, October 11, 2016 9:15 PM To: muquit/mailsend mailsend@noreply.github.com Cc: Andrew Zimmerman andrew@abcsoftek.com; Comment comment@noreply.github.com Subject: Re: [muquit/mailsend] mailsend not working with smtp.live.com (#100)

Hello,

Thank you for the info. I tried the -ehlo with hotmail.com but still cannot make it work. I have mailsend compiled with OpenSSL 0.9.8k. Could that be the problem, maybe too old?

The password has lots of weird characters like &$#! etc, could that be an issue?

For a work around, I have mailsend sending to a gmail account which forwards to a microsoft exchange email server

Connecting to smtp.live.com:587 Will detect IPv4 or IPv6 automatically

libmsock: using getaddrinfo AF_INET IPv4 IPv4 address: 65.55.163.152 EINPROGRESS=115,EWOULDBLOCK=11 connect(): socket=3,rc=-1, errno=115 Try socket 3 Setting read timeout to: 5 seconds [S] 220 BLU437-SMTP32.smtp.hotmail.com Microsoft ESMTP MAIL Service, Version: 8.0.9200.16384 ready at Tue, 11 Oct 2016 18:01:34 -0700 [C] EHLO localhost Setting read timeout to: 5 seconds [S] 250-BLU437-SMTP32.smtp.hotmail.com Hello [XXXXXXXXXXXXXXXXX] Setting read timeout to: 5 seconds [S] 250-TURN Setting read timeout to: 5 seconds [S] 250-SIZE 41943040 Setting read timeout to: 5 seconds [S] 250-ETRN Setting read timeout to: 5 seconds [S] 250-PIPELINING Setting read timeout to: 5 seconds [S] 250-DSN Setting read timeout to: 5 seconds [S] 250-ENHANCEDSTATUSCODES Setting read timeout to: 5 seconds [S] 250-8bitmime Setting read timeout to: 5 seconds [S] 250-BINARYMIME Setting read timeout to: 5 seconds [S] 250-CHUNKING Setting read timeout to: 5 seconds [S] 250-VRFY Setting read timeout to: 5 seconds [S] 250-TLS Setting read timeout to: 5 seconds [S] 250-STARTTLS Setting read timeout to: 5 seconds [S] 250 OK [C] STARTTLS Setting read timeout to: 5 seconds [S] 220 2.0.0 SMTP server ready Cipher: AES256-SHA Certificate information: Subject: /C=US/ST=Washington/L=Redmond/O=Microsoft Corporation/CN=*.hotmail.com Issuer: /C=BE/O=GlobalSign nv-sa/CN=GlobalSign Organization Validation CA - SHA256 - G2 [C] EHLO localhost [S] 250-BLU437-SMTP32.smtp.hotmail.com Hello [XXXXXXXXXXXXXX] [S] 250-TURN [S] 250-SIZE 41943040 [S] 250-ETRN [S] 250-PIPELINING [S] 250-DSN [S] 250-ENHANCEDSTATUSCODES [S] 250-8bitmime [S] 250-BINARYMIME [S] 250-CHUNKING [S] 250-VRFY [S] 250-AUTH LOGIN PLAIN XOAUTH2 [S] 250 OK Using AUTH LOGIN [C] AUTH LOGIN [S] 334 XXXXXXXXXXXXXXXXXX [C] XXXXXXXXXXXXXXXXXXXXXX [S] 334 XXXXXXXXXXXXXXXXXX [C] XXXXXXXXXXXXXXXXXXXXXX [S] 535 5.0.0 Authentication Failed Error: AUTH LOGIN failed: '535 5.0.0 Authentication Failed' Could not send mail

Dan Pattison

On 10/11/2016 5:21 PM, AndrewZim wrote:

I found I need to use -ehlo with office365.

— You are receiving this because you authored the thread. Reply to this email directly, view it on GitHub

https://github.com/muquit/mailsend/issues/100#issuecomment-253084844, or mute the thread

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AndrewZim commented 7 years ago

I don’t compile it. I just download from here: https://github.com/muquit/mailsend/releases/

Andrew Zimmerman ABC Softek LLC andrew@abcsoftek.commailto:andrew@abcsoftek.com www.SimplifyMyBiz.comhttp://www.simplifymybiz.com/

From: SirDan1963 [mailto:notifications@github.com] Sent: Wednesday, October 12, 2016 11:26 AM To: muquit/mailsend mailsend@noreply.github.com Cc: Andrew Zimmerman andrew@abcsoftek.com; Comment comment@noreply.github.com Subject: Re: [muquit/mailsend] mailsend not working with smtp.live.com (#100)

Hi Andrew,

I tried all of your suggestions, still no go. It must be something on my end, but I have no idea what. The only thing I keep coming back to is my older version of openssl. For now my work around of sending to a gmail account and having it forward to an MS exchange server is a working cludge. Thanks for all your suggestions.

Regards,

Dan Pattison EtherTek Circuits

On 10/12/2016 7:09 AM, AndrewZim wrote:

By the way, your command line works fine with my Office365 service.

Andrew Zimmerman ABC Softek LLC andrew@abcsoftek.commailto:andrew@abcsoftek.com www.SimplifyMyBiz.comhttp://www.simplifymybiz.com/

From: SirDan1963 [mailto:notifications@github.com] Sent: Wednesday, October 12, 2016 9:53 AM To: muquit/mailsend mailsend@noreply.github.com Cc: Andrew Zimmerman andrew@abcsoftek.com; Comment comment@noreply.github.com Subject: Re: [muquit/mailsend] mailsend not working with smtp.live.com (#100)

Hello Andrew,

The command line syntax below.

mailsend -to some@hotmailaddress.com -from RMS300@somewhere.ca -starttls -port 587 -auth -smtp smtp.live.com -sub test -v -user myhotmailaccount@hotmail.com -pass "#################" -ehlo

Thank you,

Dan Pattison EtherTek Circuits

On 10/12/2016 5:06 AM, AndrewZim wrote:

Can you provide your command line syntax? I use -ehlo -auth -starttls with smtp.office365.com.

Andrew Zimmerman ABC Softek LLC andrew@abcsoftek.commailto:andrew@abcsoftek.com www.SimplifyMyBiz.comhttp://www.simplifymybiz.com/

From: SirDan1963 [mailto:notifications@github.com] Sent: Tuesday, October 11, 2016 9:15 PM To: muquit/mailsend mailsend@noreply.github.com Cc: Andrew Zimmerman andrew@abcsoftek.com; Comment comment@noreply.github.com Subject: Re: [muquit/mailsend] mailsend not working with smtp.live.com (#100)

Hello,

Thank you for the info. I tried the -ehlo with hotmail.com but still cannot make it work. I have mailsend compiled with OpenSSL 0.9.8k. Could that be the problem, maybe too old?

The password has lots of weird characters like &$#! etc, could that be an issue?

For a work around, I have mailsend sending to a gmail account which forwards to a microsoft exchange email server

Connecting to smtp.live.com:587 Will detect IPv4 or IPv6 automatically

libmsock: using getaddrinfo AF_INET IPv4 IPv4 address: 65.55.163.152 EINPROGRESS=115,EWOULDBLOCK=11 connect(): socket=3,rc=-1, errno=115 Try socket 3 Setting read timeout to: 5 seconds [S] 220 BLU437-SMTP32.smtp.hotmail.com Microsoft ESMTP MAIL Service, Version: 8.0.9200.16384 ready at Tue, 11 Oct 2016 18:01:34 -0700 [C] EHLO localhost Setting read timeout to: 5 seconds [S] 250-BLU437-SMTP32.smtp.hotmail.com Hello [XXXXXXXXXXXXXXXXX] Setting read timeout to: 5 seconds [S] 250-TURN Setting read timeout to: 5 seconds [S] 250-SIZE 41943040 Setting read timeout to: 5 seconds [S] 250-ETRN Setting read timeout to: 5 seconds [S] 250-PIPELINING Setting read timeout to: 5 seconds [S] 250-DSN Setting read timeout to: 5 seconds [S] 250-ENHANCEDSTATUSCODES Setting read timeout to: 5 seconds [S] 250-8bitmime Setting read timeout to: 5 seconds [S] 250-BINARYMIME Setting read timeout to: 5 seconds [S] 250-CHUNKING Setting read timeout to: 5 seconds [S] 250-VRFY Setting read timeout to: 5 seconds [S] 250-TLS Setting read timeout to: 5 seconds [S] 250-STARTTLS Setting read timeout to: 5 seconds [S] 250 OK [C] STARTTLS Setting read timeout to: 5 seconds [S] 220 2.0.0 SMTP server ready Cipher: AES256-SHA Certificate information: Subject: /C=US/ST=Washington/L=Redmond/O=Microsoft Corporation/CN=*.hotmail.com Issuer: /C=BE/O=GlobalSign nv-sa/CN=GlobalSign Organization Validation CA - SHA256 - G2 [C] EHLO localhost [S] 250-BLU437-SMTP32.smtp.hotmail.com Hello [XXXXXXXXXXXXXX] [S] 250-TURN [S] 250-SIZE 41943040 [S] 250-ETRN [S] 250-PIPELINING [S] 250-DSN [S] 250-ENHANCEDSTATUSCODES [S] 250-8bitmime [S] 250-BINARYMIME [S] 250-CHUNKING [S] 250-VRFY [S] 250-AUTH LOGIN PLAIN XOAUTH2 [S] 250 OK Using AUTH LOGIN [C] AUTH LOGIN [S] 334 XXXXXXXXXXXXXXXXXX [C] XXXXXXXXXXXXXXXXXXXXXX [S] 334 XXXXXXXXXXXXXXXXXX [C] XXXXXXXXXXXXXXXXXXXXXX [S] 535 5.0.0 Authentication Failed Error: AUTH LOGIN failed: '535 5.0.0 Authentication Failed' Could not send mail

Dan Pattison

On 10/11/2016 5:21 PM, AndrewZim wrote:

I found I need to use -ehlo with office365.

— You are receiving this because you authored the thread. Reply to this email directly, view it on GitHub

https://github.com/muquit/mailsend/issues/100#issuecomment-253084844, or mute the thread

https://github.com/notifications/unsubscribe-auth/AHk-h_7THbqDI0ANqH6eS_jiwutV80khks5qzCgigaJpZM4J6Fgf.

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muquit commented 7 years ago

As you are running on Linux, use single quotes around your password, otherwise if there is any special character like $ in your password, shell will expand it. Thanks

SirDan1963 commented 7 years ago

Thank you! That fixed it!

Dan Pattison EtherTek Circuits

On 10/12/2016 10:59 AM, muquit wrote:

As you are running on Linux, use single quotes around your password, otherwise if there is any special character like $ in your password, shell will expand it. Thanks

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christopherccg commented 3 years ago

mailsend.exe -v +cc +bc -4 -ehlo -starttls -auth -smtp smtp.office365.com -port 587 -sub "ASUNTO" -t CORREOALQUEVA -user CORREOQUIENENVIA -pass "CONTRASEÑA" -f CORREOQUIENENVIA

Así me funcionó a mi.

Gracias por su ayuda.

atesin commented 1 year ago

for god sake... dont use "EHLO localhost" or you could be blocked

more info = https://github.com/muquit/mailsend/issues/132#issuecomment-1637013321