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login to smtp.mail.yahoo.com failed

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I have created a Yahoo mail account and configured it in Thunderbird correctly according to the Yahoo (https://help.yahoo.com/kb/SLN3773.html) and Mozilla (http://kb.mozillazine.org/Yahoo) docs.

I can access IMAP without any problem but SMTP always fails. I've checked the config repeatedly, deleted and re-added the password in Thunderbird, changed the Yahoo password and reconfigured Thunderbird yet again, disabled and re-enabled Yahoo's 'insecure' mail access option, all without any success. Every time I try to send an email via Yahoo on port 465 I get the same error 'login to smtp.mail.yahoo.com failed'. If I try with port 587 it just times out. I tried OAuth2 authentication but that failed as well.

I have no idea how to proceed from here.

This is the Thunderbird 'Troubleshooting Information' (without the 'Important Modified Preferences' because they won't fit in this text box):

 Application Basics
   Name: Thunderbird
   Version: 52.2.1
   User Agent: Mozilla/5.0 (X11; Linux x86_64; rv:52.0) Gecko/20100101 Thunderbird/52.2.1
   Profile Directory: Open Directory
             (Local drive)
   Application Build ID: 20170626135948
   Enabled Plugins: about:plugins
   Build Configuration: about:buildconfig
   Memory Use: about:memory
   Profiles: about:profiles
 Mail and News Accounts
   account2:
     INCOMING: account2, , (none) Local Folders, plain, passwordCleartext
   account18:
     INCOMING: account18, , (imap) imap.googlemail.com:993, SSL, passwordCleartext
     OUTGOING: , smtp.googlemail.com:465, SSL, passwordCleartext, true
   account24:
     INCOMING: account24, , (imap) imap.googlemail.com:993, SSL, passwordCleartext
     OUTGOING: , smtp.googlemail.com:465, SSL, passwordCleartext, true
   account25:
     INCOMING: account25, , (imap) imap.googlemail.com:993, SSL, passwordCleartext
     OUTGOING: , smtp.googlemail.com:465, SSL, passwordCleartext, true
   account27:
     INCOMING: account27, , (imap) imap.gmail.com:993, SSL, passwordCleartext
     OUTGOING: , smtp.gmail.com:465, SSL, OAuth2, true
   account28:
     INCOMING: account28, , (imap) imap.gmail.com:993, SSL, passwordCleartext
     OUTGOING: , smtp.gmail.com:465, SSL, OAuth2, true
   account30:
     INCOMING: account30, , (imap) imap.openmailbox.org:143, alwaysSTARTTLS, passwordCleartext
     OUTGOING: , smtp.openmailbox.org:465, SSL, passwordCleartext, true
     OUTGOING: , smtp.openmailbox.org:465, SSL, passwordCleartext, false
     OUTGOING: , smtp.openmailbox.org:465, SSL, passwordCleartext, false
     OUTGOING: , smtp.openmailbox.org:465, SSL, passwordCleartext, false
     OUTGOING: , smtp.openmailbox.org:465, SSL, passwordCleartext, false
   account31:
     INCOMING: account31, , (imap) imap.mail.yahoo.com:993, SSL, passwordCleartext
     OUTGOING: , smtp.mail.yahoo.com:465, SSL, passwordCleartext, true
 Crash Reports
 Extensions
   CompactHeader, 2.1.0, true, {58D4392A-842E-11DE-B51A-C7B855D89593}
   Enigmail, 1.9.8.1, true, {847b3a00-7ab1-11d4-8f02-006008948af5}
   ImportExportTools, 3.2.4.1, true, {3ed8cc52-86fc-4613-9026-c1ef969da4c3}
   Manually sort folders, 1.1.1, true, tbsortfolders@xulforum.org
   PrintingTools, 1.2.5, true, {5e9999c2-ba1d-44b6-bcee-5b30ce37d3b0}
   Remove Duplicate Messages, 0.1.14, true, {12345678-1234-1234-1234-123456789abc}
   Super Date Format, 1.1, true, superdateformat@buildontechnologies.com
   ConfigDate, 0.7.5, false, {782E3D25-61FD-4997-AA8F-D3F18FA92ECC}
   DOM Inspector, 2.0.16.1-signed, false, inspector@mozilla.org
   Is It Compatible?, 0.5.3.1-signed.1-signed, false, isitcompatible@eternicode.com
   Messaging Menu and Unity Launcher integration, 1.3.1, false, messagingmenu@mozilla.com


 Graphics
     GPU #1
     Description: NVIDIA Corporation -- GeForce GTX 970/PCIe/SSE2
     Vendor ID: NVIDIA Corporation
     Device ID: GeForce GTX 970/PCIe/SSE2
     Driver Version: 4.5.0 NVIDIA 384.59
     Features
     WebGL Renderer: NVIDIA Corporation -- GeForce GTX 970/PCIe/SSE2 -- 4.5.0 NVIDIA 384.59
     AzureCanvasBackend: skia
     AzureCanvasAccelerated: 0
     AzureFallbackCanvasBackend: none
     AzureContentBackend: skia
     CairoUseXRender: 0
 JavaScript
 Incremental GC: 1
 Accessibility
   Activated: 0
   Prevent Accessibility: 0
 Library Versions
     Expected minimum version
     Version in use
     NSPR
     4.13.1
     4.13.1
     NSS
     3.28.5
     3.28.5
     NSS Util
     3.28.5
     3.28.5
     NSS SSL
     3.28.5
     3.28.5
     NSS S/MIME
     3.28.5
     3.28.5
I have created a Yahoo mail account and configured it in Thunderbird correctly according to the Yahoo (https://help.yahoo.com/kb/SLN3773.html) and Mozilla (http://kb.mozillazine.org/Yahoo) docs. I can access IMAP without any problem but SMTP always fails. I've checked the config repeatedly, deleted and re-added the password in Thunderbird, changed the Yahoo password and reconfigured Thunderbird yet again, disabled and re-enabled Yahoo's 'insecure' mail access option, all without any success. Every time I try to send an email via Yahoo on port 465 I get the same error 'login to smtp.mail.yahoo.com failed'. If I try with port 587 it just times out. I tried OAuth2 authentication but that failed as well. I have no idea how to proceed from here. This is the Thunderbird 'Troubleshooting Information' (without the 'Important Modified Preferences' because they won't fit in this text box): Application Basics Name: Thunderbird Version: 52.2.1 User Agent: Mozilla/5.0 (X11; Linux x86_64; rv:52.0) Gecko/20100101 Thunderbird/52.2.1 Profile Directory: Open Directory (Local drive) Application Build ID: 20170626135948 Enabled Plugins: about:plugins Build Configuration: about:buildconfig Memory Use: about:memory Profiles: about:profiles Mail and News Accounts account2: INCOMING: account2, , (none) Local Folders, plain, passwordCleartext account18: INCOMING: account18, , (imap) imap.googlemail.com:993, SSL, passwordCleartext OUTGOING: , smtp.googlemail.com:465, SSL, passwordCleartext, true account24: INCOMING: account24, , (imap) imap.googlemail.com:993, SSL, passwordCleartext OUTGOING: , smtp.googlemail.com:465, SSL, passwordCleartext, true account25: INCOMING: account25, , (imap) imap.googlemail.com:993, SSL, passwordCleartext OUTGOING: , smtp.googlemail.com:465, SSL, passwordCleartext, true account27: INCOMING: account27, , (imap) imap.gmail.com:993, SSL, passwordCleartext OUTGOING: , smtp.gmail.com:465, SSL, OAuth2, true account28: INCOMING: account28, , (imap) imap.gmail.com:993, SSL, passwordCleartext OUTGOING: , smtp.gmail.com:465, SSL, OAuth2, true account30: INCOMING: account30, , (imap) imap.openmailbox.org:143, alwaysSTARTTLS, passwordCleartext OUTGOING: , smtp.openmailbox.org:465, SSL, passwordCleartext, true OUTGOING: , smtp.openmailbox.org:465, SSL, passwordCleartext, false OUTGOING: , smtp.openmailbox.org:465, SSL, passwordCleartext, false OUTGOING: , smtp.openmailbox.org:465, SSL, passwordCleartext, false OUTGOING: , smtp.openmailbox.org:465, SSL, passwordCleartext, false account31: INCOMING: account31, , (imap) imap.mail.yahoo.com:993, SSL, passwordCleartext OUTGOING: , smtp.mail.yahoo.com:465, SSL, passwordCleartext, true Crash Reports Extensions CompactHeader, 2.1.0, true, {58D4392A-842E-11DE-B51A-C7B855D89593} Enigmail, 1.9.8.1, true, {847b3a00-7ab1-11d4-8f02-006008948af5} ImportExportTools, 3.2.4.1, true, {3ed8cc52-86fc-4613-9026-c1ef969da4c3} Manually sort folders, 1.1.1, true, tbsortfolders@xulforum.org PrintingTools, 1.2.5, true, {5e9999c2-ba1d-44b6-bcee-5b30ce37d3b0} Remove Duplicate Messages, 0.1.14, true, {12345678-1234-1234-1234-123456789abc} Super Date Format, 1.1, true, superdateformat@buildontechnologies.com ConfigDate, 0.7.5, false, {782E3D25-61FD-4997-AA8F-D3F18FA92ECC} DOM Inspector, 2.0.16.1-signed, false, inspector@mozilla.org Is It Compatible?, 0.5.3.1-signed.1-signed, false, isitcompatible@eternicode.com Messaging Menu and Unity Launcher integration, 1.3.1, false, messagingmenu@mozilla.com Graphics GPU #1 Description: NVIDIA Corporation -- GeForce GTX 970/PCIe/SSE2 Vendor ID: NVIDIA Corporation Device ID: GeForce GTX 970/PCIe/SSE2 Driver Version: 4.5.0 NVIDIA 384.59 Features WebGL Renderer: NVIDIA Corporation -- GeForce GTX 970/PCIe/SSE2 -- 4.5.0 NVIDIA 384.59 AzureCanvasBackend: skia AzureCanvasAccelerated: 0 AzureFallbackCanvasBackend: none AzureContentBackend: skia CairoUseXRender: 0 JavaScript Incremental GC: 1 Accessibility Activated: 0 Prevent Accessibility: 0 Library Versions Expected minimum version Version in use NSPR 4.13.1 4.13.1 NSS 3.28.5 3.28.5 NSS Util 3.28.5 3.28.5 NSS SSL 3.28.5 3.28.5 NSS S/MIME 3.28.5 3.28.5

Chosen solution

I eventually stumbled on the solution myself: password length.

I was using a 36-random-character password (generated by KeePassX) for my Yahoo mail. That worked ok for web login and IMAP, but it was too long for Yahoo's SMTP server. No idea why, it doesn't make sense to me why it would work for some protocols but not others.

Anyway, when I changed my Yahoo account to a 24-random-character password SMTP started working.

I have since found a forum post stating that the maximum length for Yahoo passwords is 32 characters, but I found no supporting info in any official Yahoo docs. Also, my 36 character password was working with web login and IMAP, so maybe it's a sign of inconsistency on the part of people at Yahoo.

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Chosen Solution

I eventually stumbled on the solution myself: password length.

I was using a 36-random-character password (generated by KeePassX) for my Yahoo mail. That worked ok for web login and IMAP, but it was too long for Yahoo's SMTP server. No idea why, it doesn't make sense to me why it would work for some protocols but not others.

Anyway, when I changed my Yahoo account to a 24-random-character password SMTP started working.

I have since found a forum post stating that the maximum length for Yahoo passwords is 32 characters, but I found no supporting info in any official Yahoo docs. Also, my 36 character password was working with web login and IMAP, so maybe it's a sign of inconsistency on the part of people at Yahoo.