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IMAP SMTP connection problem with Exchange 2010 #130

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InfopactMLoos opened this issue Oct 11, 2017 · 35 comments
Closed

IMAP SMTP connection problem with Exchange 2010 #130

InfopactMLoos opened this issue Oct 11, 2017 · 35 comments
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@InfopactMLoos
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InfopactMLoos commented Oct 11, 2017

I tried to enable the IMAP provider but I ran into issues somehow. I tried to connect to my works exchange server through IMAP protocol, which should work as it does so with other clients.

It seems the Incoming mail (IMAP) is ok, however the SMTP part apparently fails. I looked a bit into SMTP protocol and as far as I understand it seems to go as planned but then abruptly aborts. SMTP code 250 should be expected and ok. The only error I see is the message: mailsmtp Last Error Code: 17. I cannot seem to find any information regarding this error code so any help is appreciated!

Are there any related issues?

I first ran into issue #123. This however seems to be another issue so I created this new ticket.

What operating system are you using?

Ubuntu 16.04

What version of Mailspring are you using?

1.0.3-f82c8836 EDIT: still broken on 1.0.7-664204d8

--

Bug?

Do you have any third-party plugins installed? If so, which ones?

No

Is the issue related to a specific email provider (Gmail, Exchange, etc.)?

IMAP (with Exchange server 2010)

Is the issue reproducible with a particular attachment, message, signature, etc?

Reproduce steps are hard to supply as it seems something related to my setup.
This is my error log, I have redacted some info.

----------IMAP----------
* OK The Microsoft Exchange IMAP4 service is ready.
1 CAPABILITY
* CAPABILITY IMAP4 IMAP4rev1 AUTH=NTLM AUTH=GSSAPI AUTH=PLAIN UIDPLUS CHILDREN IDLE NAMESPACE LITERAL+
1 OK CAPABILITY completed.
2 LOGIN "MYUSERNAME" *********
2 OK LOGIN completed.
3 CAPABILITY
* CAPABILITY IMAP4 IMAP4rev1 AUTH=NTLM AUTH=GSSAPI AUTH=PLAIN UIDPLUS CHILDREN IDLE NAMESPACE LITERAL+
3 OK CAPABILITY completed.
4 NAMESPACE
* NAMESPACE (("" "/")) NIL NIL
4 OK NAMESPACE completed.
5 LIST "" "*"
* LIST (\HasNoChildren) "/" Agenda
* LIST (\HasNoChildren) "/" Concepten
* LIST (\HasChildren) "/" Contactpersonen
* LIST (\Marked \HasNoChildren) "/" "Contactpersonen/Lync Contacts"
* LIST (\HasNoChildren) "/" "Conversation History"
* LIST (\HasNoChildren) "/" Drafts
* LIST (\HasNoChildren) "/" "Infected Items"
* LIST (\HasNoChildren) "/" Journaal
* LIST (\HasNoChildren) "/" Junk
* LIST (\HasNoChildren) "/" Notities
* LIST (\HasNoChildren) "/" "Ongewenste e-mail"
* LIST (\Marked \HasChildren) "/" INBOX
5 OK LIST completed.


----------SMTP----------
220 SERVERDOMAIN Microsoft ESMTP MAIL Service ready at Wed, 11 Oct 2017 15:15:07 +0200
���EHLO MYPC
250-SERVERDOMAIN Hello [SERVERIP]
250-SIZE 104857600
250-PIPELINING
250-DSN
250-ENHANCEDSTATUSCODES
250-STARTTLS
250-AUTH GSSAPI NTLM
250-8BITMIME
250-BINARYMIME
250 CHUNKING
STARTTLS
��220 2.0.0 SMTP server ready
EHLO MYPC
250-SERVERDOMAIN Hello [SERVERIP]
250-SIZE 104857600
250-PIPELINING
250-DSN
250-ENHANCEDSTATUSCODES
250-AUTH GSSAPI NTLM LOGIN
250-8BITMIME
250-BINARYMIME
250 CHUNKING

SMTP Last Response Code: 250

SMTP Last Response: SERVERDOMAIN Hello [SERVERIP]
SIZE 104857600
PIPELINING
DSN
ENHANCEDSTATUSCODES
AUTH GSSAPI NTLM LOGIN
8BITMIME
BINARYMIME
CHUNKING


mailsmtp Last Error Code: 17

mailsmtp Last Error Location: 10

--

@bengotow
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Hey there—this looks like a certificate error. The logs aren't much use because the client hangs up due to the certificate error before even trying to log in. Can you look at #144 and see if the file paths that are referenced there are valid for you? I'm surprised this is happening on Ubuntu actually.

@thob
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thob commented Oct 17, 2017

hmm, in etc/ssl/certs are also links to /usr/share/ca-certificates/mozilla/

@bengotow
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That's probably unrelated. Can you see if any of these paths are valid on your system? Mailspring needs to be able to find the crt or pem file in one of the paths below. If it's somewhere else, we'll need to update it.

        // Debian, Ubuntu, Arch: maintained by update-ca-certificates
        "/etc/ssl/certs/ca-certificates.crt",
        // Red Hat 5+, Fedora, Centos
        "/etc/pki/tls/certs/ca-bundle.crt",
        // Red Hat 4
        "/usr/share/ssl/certs/ca-bundle.crt",
        // FreeBSD (security/ca-root-nss package)
        "/usr/local/share/certs/ca-root-nss.crt",
        // FreeBSD (deprecated security/ca-root package, removed 2008)
        "/usr/local/share/certs/ca-root.crt",
        // FreeBSD (optional symlink)
        // OpenBSD
        "/etc/ssl/cert.pem",

@thob
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thob commented Oct 17, 2017

ca-certificates.crt is in /etc/ssl/certs, no cert.pem

@InfopactMLoos
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Sorry been to busy at work today, hopefully I can check tomorrow.

@InfopactMLoos
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InfopactMLoos commented Oct 18, 2017

Certs seems to be at the given ubuntu path as expected:

ls -l /etc/ssl/certs/ca-certificates.crt
-rw-r--r-- 1 root root 233394 okt 3 19:23 /etc/ssl/certs/ca-certificates.crt

Also when I use curl I get no cert errors at all.

And a more verbose check:

openssl s_client -connect REDACTED_DOMAIN:443
CONNECTED(00000003)
depth=3 C = SE, O = AddTrust AB, OU = AddTrust External TTP Network, CN = AddTrust External CA Root
verify return:1
depth=2 C = GB, ST = Greater Manchester, L = Salford, O = COMODO CA Limited, CN = COMODO RSA Certification Authority
verify return:1
depth=1 C = GB, ST = Greater Manchester, L = Salford, O = COMODO CA Limited, CN = COMODO RSA Domain Validation Secure Server CA
verify return:1
depth=0 OU = Domain Control Validated, OU = PositiveSSL Multi-Domain, CN = REDACTED_DOMAIN
verify return:1
---
Certificate chain
 0 s:/OU=Domain Control Validated/OU=PositiveSSL Multi-Domain/CN=REDACTED_DOMAIN
   i:/C=GB/ST=Greater Manchester/L=Salford/O=COMODO CA Limited/CN=COMODO RSA Domain Validation Secure Server CA
 1 s:/C=GB/ST=Greater Manchester/L=Salford/O=COMODO CA Limited/CN=COMODO RSA Domain Validation Secure Server CA
   i:/C=GB/ST=Greater Manchester/L=Salford/O=COMODO CA Limited/CN=COMODO RSA Certification Authority
 2 s:/C=GB/ST=Greater Manchester/L=Salford/O=COMODO CA Limited/CN=COMODO RSA Certification Authority
   i:/C=SE/O=AddTrust AB/OU=AddTrust External TTP Network/CN=AddTrust External CA Root
---
Server certificate
-----BEGIN CERTIFICATE-----
MIIFgjCCBGqgAwIBAgIQLKkxsSW1pR0u3O2yNkcmBDANBgkqhkiG9w0BAQsFADCB
kDELMAkGA1UEBhMCR0IxGzAZBgNVBAgTEkdyZWF0ZXIgTWFuY2hlc3RlcjEQMA4G
A1UEBxMHU2FsZm9yZDEaMBgGA1UEChMRQ09NT0RPIENBIExpbWl0ZWQxNjA0BgNV
BAMTLUNPTU9ETyBSU0EgRG9tYWluIFZhbGlkYXRpb24gU2VjdXJlIFNlcnZlciBD
QTAeFw0xNjAxMTEwMDAwMDBaFw0xOTAyMDQyMzU5NTlaMGQxITAfBgNVBAsTGERv
bWFpbiBDb250cm9sIFZhbGlkYXRlZDEhMB8GA1UECxMYUG9zaXRpdmVTU0wgTXVs
dGktRG9tYWluMRwwGgYDVQQDExNvdXRsb29rLmluZm9wYWN0Lm5sMIIBIjANBgkq
hkiG9w0BAQEFAAOCAQ8AMIIBCgKCAQEAqTsohfRbF/9yaupjFcKEu51zF46Cszab
iM7LQWw2MKK9TBHoXyodUrrzEGloIxL0KC7j+fXWNp4x3VV62FCQNb8Kc8Q1XC2T
aH7W84ranctYKwXdRetwkzWoa0ElLdXcAq+R0NVerkhGgoLZ+Nmp8xFb3KiSvZ5O
F1hvuxyMXe28+g/UB+Db5ms7Liev6G50Q0B0H+y56UnaebR2apbI3AR8BF/lbl7m
9aiKXsJQhPUW8Z3kNYE8x1Q7lQSpeAbQtaaCzdmfpDiHx2xchr5tUD6fOKfN9pH2
t+jxWsYDL4XQxRyZl3Uw830ApS9B449lVMDgoklhyrMZa9OUmrpTjwIDAQABo4IC
ATCCAf0wHwYDVR0jBBgwFoAUkK9qOpRaC9iQ6hJWc99DtDoo2ucwHQYDVR0OBBYE
FPPzUbp9IyZc1jcfRwjO6FM+Tj6BMA4GA1UdDwEB/wQEAwIFoDAMBgNVHRMBAf8E
AjAAMB0GA1UdJQQWMBQGCCsGAQUFBwMBBggrBgEFBQcDAjBPBgNVHSAESDBGMDoG
CysGAQQBsjEBAgIHMCswKQYIKwYBBQUHAgEWHWh0dHBzOi8vc2VjdXJlLmNvbW9k
by5jb20vQ1BTMAgGBmeBDAECATBUBgNVHR8ETTBLMEmgR6BFhkNodHRwOi8vY3Js
LmNvbW9kb2NhLmNvbS9DT01PRE9SU0FEb21haW5WYWxpZGF0aW9uU2VjdXJlU2Vy
dmVyQ0EuY3JsMIGFBggrBgEFBQcBAQR5MHcwTwYIKwYBBQUHMAKGQ2h0dHA6Ly9j
cnQuY29tb2RvY2EuY29tL0NPTU9ET1JTQURvbWFpblZhbGlkYXRpb25TZWN1cmVT
ZXJ2ZXJDQS5jcnQwJAYIKwYBBQUHMAGGGGh0dHA6Ly9vY3NwLmNvbW9kb2NhLmNv
bTBPBgNVHREESDBGghNvdXRsb29rLmluZm9wYWN0Lm5sghhhdXRvZGlzY292ZXIu
aW5mb3BhY3QubmyCFWV4YzAxLmludC5pbmZvcGFjdC5ubDANBgkqhkiG9w0BAQsF
AAOCAQEAHR8OPF9734qWIF+Dm3tHGuLN3vGjAB5V/pS5CgBVKqrpc8kvHnmHfLY8
hnkM8NowY4DoeG3s0vr0gY1lLxkpX4smnwKyjO10Gx9GApq2Rzg9RxkgpzmtO+oS
kgb50eC5dIcTkpMCklbvRRKlB2qC2vz5wzNFbj2e7EO4zADCeA54BKi21sTAWwHO
6iANMsjwJNz2/8M81LtTHeD+FI9RdS2pxv96e21l1K8iAz/OELmt1eiFqILguxoT
W+nud8LMxWHKNThXuV+iUkfxDDIwZ+0adkfEWYqpEDu1R6e6sc4vgnWrznw7P5ks
Pkc95LIXK/1EwyoCSTW5r83w2gcScg==
-----END CERTIFICATE-----
subject=/OU=Domain Control Validated/OU=PositiveSSL Multi-Domain/CN=REDACTED_DOMAIN
issuer=/C=GB/ST=Greater Manchester/L=Salford/O=COMODO CA Limited/CN=COMODO RSA Domain Validation Secure Server CA
---
No client certificate CA names sent
Server Temp Key: ECDH, P-256, 256 bits
---
SSL handshake has read 4858 bytes and written 439 bytes
---
New, TLSv1/SSLv3, Cipher is ECDHE-RSA-AES256-SHA
Server public key is 2048 bit
Secure Renegotiation IS supported
Compression: NONE
Expansion: NONE
No ALPN negotiated
SSL-Session:
    Protocol  : TLSv1
    Cipher    : ECDHE-RSA-AES256-SHA
    Session-ID: 8F300000AC27AB0646550EC71887D9F5EF7ACAA3052CD11C5C8F565EDD5914B1
    Session-ID-ctx: 
    Master-Key: 87298DD272E3A99417ABB247EC935CEBD910E4EBE6D851ED2C1C46676B6C38A85C36E003DEF8B0AF5F957742CED9672C
    Key-Arg   : None
    PSK identity: None
    PSK identity hint: None
    SRP username: None
    Start Time: 1508317808
    Timeout   : 300 (sec)
    Verify return code: 0 (ok)
---

@LiHRaM
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LiHRaM commented Oct 18, 2017

Been having the same issue with school and work accounts. Running Ubuntu 16.04, and had no trouble finding the cert file at the given paths.

@thob
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thob commented Oct 18, 2017

let me add that I had no issues with Linux Mint 18.2 (Mate) and Ubuntu 16.04, only on LM 17.3 i get the error

@InfopactMLoos
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Then I am suspecting that it does not have to do with Ubuntu versions. Did you get the same mailsping versions to work with mint 18.2 and ubuntu 16.04 as you had fail with mint 17.3?

@InfopactMLoos
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@bengotow is it possible to download older build versions?

@DaichiUeura
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DaichiUeura commented Oct 24, 2017

Probably I faced the same issue on macOS when trying to connect to my company's Exchange server via IMAP and SMTP protocol. The app said 'Authentication Error - Check your username and password. (SMTP)View Log'. In my case, the SMTP server doesn't require authentication.

BTW, would it be possible to bypass SMTP configuration? I would like to see my inbox as a first step.

----------SMTP----------
220 <snip> Microsoft ESMTP MAIL Service ready at Tue, 24 Oct 2017 03:01:51 +0000
EHLO <snip>
250-<snip> Hello [<snip>]
250-SIZE 20971520
250-PIPELINING
250-DSN
250-ENHANCEDSTATUSCODES
250-STARTTLS
250-AUTH GSSAPI NTLM
250-8BITMIME
250-BINARYMIME
250 CHUNKING

SMTP Last Response Code: 250

SMTP Last Response: <snip> Hello [<snip>]
SIZE 20971520
PIPELINING
DSN
ENHANCEDSTATUSCODES
STARTTLS
AUTH GSSAPI NTLM
8BITMIME
BINARYMIME
CHUNKING


mailsmtp Last Error Code: 17

mailsmtp Last Error Location: 10

What operating system are you using?

OS X El Capitan 10.11.6

What version of Mailspring are you using?

1.0.6

@thomaswieland
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I can confirm what DaichiUeura is telling. IMAP (Exchange) works fine, but SMTP-Setup against an Unix/Linux SMTP Server (no auth, white-listed source IP address) prevents me from finishing setup. Error message is the same (mailsmtp Last Error Code: 17).

@DaichiUeura
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mailsmtp Last Error Code: 17 and mailsmtp Last Error Location: 10 might appear in several different cases(no authentication is required in my case but it seems certificate stuff is being discussed here)? If so, I should have filed a new issue.

@ghost
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ghost commented Oct 24, 2017

mailsmtp Last Error Code: 17 mailsmtp Last Error Location: 10
Same error on Arch Linux. Version: 1.0.6-9448c884

@InfopactMLoos
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@DaichiUeura maybe, @bengotow pointed me towards certificates, however this has not lead me to any conclusive results as of now. Other people who added to my report have all reported different variables in their exposure to the same error message. This makes me think that the error code is a very common one. I would like to do more detailed research to better pin point the exact cause. However I have no idea where to check further, my knowledge of the codebase is practically none and my knowledge of the SMTP protocol is rudimentary. If anyone with better knowledge knows where to check further I would gladly do so, any help appreciated!

@aia832003
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aia832003 commented Oct 28, 2017

I am having similar issues on latest version running on Fedora 26. I can confirm that original Nylas Mail is working.

@InfopactMLoos
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InfopactMLoos commented Oct 31, 2017

Ok I followed the following tutorial to test the connection from the command line: https://halon.io/blog/how-to-test-smtp-servers-using-the-command-line/. Everything is working fine with the exact same credentials and server info as I use in Mailspring so I think it is save to assume there is something bugged in Mailspring. @bengotow is there anything I can supply to help fix this issue? Please let me know because I would really like to use this client, I loved Nylas so I must have the same love for its offspring :).

EDIT Added below part
As I compare the results from my tests (btw I have now also tested with swaks, swiss army knife SMTP, same successful result as with openssl) I notice that according to mailspring logs it never sends the AUTH LOGIN command to the SMTP server. It does send the STARTTLS command which receive a successful 220 2.0.0 SMTP server ready so I think the TLS handshake is successful but Mailspring is not able to determine the next course of action. Maybe it does not receive the expected response?

@KalSat
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KalSat commented Nov 7, 2017

I have the same problem on Ubuntu 17.10, but Geary is working.

@InfopactMLoos
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@bengotow, please some feedback on my questions? I would happily fix it with a pull request but no idea where to begin. Where does the IMAP authentication take place?

@bengotow
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bengotow commented Nov 7, 2017

Hey folks—sorry for the delay. Yeah—it looks like there are several different issues being reported here. Support for SMTP without authentication (re @DaichiUeura and @thomaswieland's comments) was added in 1.0.3—file a separate issue if you're still having trouble with that.

It's not really documented anywhere, but the mailsmtp Last Error Code being printed by Mailspring corresponds to an enum index in this table: https://github.com/dinhviethoa/libetpan/blob/master/src/low-level/smtp/mailsmtp_types.h#L48. It looks like value 17 is MAILSMTP_ERROR_AUTH_LOGIN, which is consistent with your latest notes.

Could you try ruling out any certificate / SSL issues by checking the "Allow Insecure SSL" box in IMAP/SMTP config? If that /does/ fix the issue, it'll narrow it down quite a bit.

@aia832003
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aia832003 commented Nov 7, 2017 via email

@InfopactMLoos
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InfopactMLoos commented Nov 7, 2017

@bengotow, "Allow Insecure SSL" makes no difference. As I said using the openssl or swaks tools to manually login works so I see no problems in certificates, also as other people have it working on Ubuntu and I don't have anything custom on my distro (using LTS since its a work laptop) I don't see any reason Mailspring should have trouble finding certificates.

@aia832003, your issue is not the same (although the error message might be the same but it is a generic one). So no This seems to be fixed is incorrect for this issue.

@InfopactMLoos InfopactMLoos changed the title IMAP SMTP authentication error? mailsmtp Last Error Code: 17 IMAP SMTP connection problem with Exchange 2010 Nov 7, 2017
@byteSamurai
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I can confirm this error using my own mail server. I have no problems using Thunderbird or Geary. But Mailspring wont connect to my SMTP-Server.

Cencosored log:

----------SMTP----------
220 mail.server.tld ESMTP Postfix (Ubuntu)
EHLO localmachine
250-mail.server.tld
250-PIPELINING
250-SIZE 26214400
250-ETRN
250-STARTTLS
250-ENHANCEDSTATUSCODES
250-8BITMIME
250 DSN
STARTTLS
er
220 2.0.0 Ready to start TLS
EHLO localmachine
250-mail.server.tld
250-PIPELINING
250-SIZE 26214400
250-ETRN
250-AUTH DIGEST-MD5 CRAM-MD5 PLAIN LOGIN
250-ENHANCEDSTATUSCODES
250-8BITMIME
250 DSN

SMTP Last Response Code: 250

SMTP Last Response: mail.server.tld
PIPELINING
SIZE 26214400
ETRN
AUTH DIGEST-MD5 CRAM-MD5 PLAIN LOGIN
ENHANCEDSTATUSCODES
8BITMIME
DSN


mailsmtp Last Error Code: 17

mailsmtp Last Error Location: 10

@InfopactMLoos
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Since my company migrated to office 365 I don't have any problem connecting mailspring to my mailbox anymore. This makes debugging this issue a bit harder and since support on this issue is also non-existing I will just close it.

@markpash
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markpash commented Dec 7, 2017

I have the exact same issue, and if it helps, it's the same on windows as well. I can help test this if needed.

@InfopactMLoos
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Since I have no mailserver to reproduce this problem with anymore, no clue where to look for more debugging information, no way to differentiate between all the different issues above and mostly because there is no support or at the least pointers on where to look in the source code.... I closed this issue and feel no need to pursue this any further. If you want help to fix the issue please create a new issue, best of luck.

@ltjdym
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ltjdym commented Dec 21, 2017

Same problem. Would have loved to keep using mailspring otherwise...

@ltjdym
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ltjdym commented Dec 21, 2017

BTW, can use newton mail without any problems... Maybe mailspring only works with outlook 365 and not outlook.com ? Or outlook exchange?

@ltjdym
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ltjdym commented Dec 21, 2017

----------IMAP----------

  • OK The Microsoft Exchange IMAP4 service is ready. [QgBOADYAUABSADEAMABDAEEAMAAwADMAOQAuAG4AYQBtAHAAcgBkADEAMAAuAHAAcgBvAGQALgBvAHUAdABsAG8AbwBrAC4AYwBvAG0A]
    ذ�S1 CAPABILITY
  • CAPABILITY IMAP4 IMAP4rev1 AUTH=PLAIN AUTH=XOAUTH2 SASL-IR UIDPLUS MOVE ID UNSELECT CHILDREN IDLE NAMESPACE LITERAL+
    1 OK CAPABILITY completed.
    2 LOGIN "xxxxx@xxxx.org" *********
    2 OK LOGIN completed.
    3 CAPABILITY
  • CAPABILITY IMAP4 IMAP4rev1 AUTH=PLAIN AUTH=XOAUTH2 SASL-IR UIDPLUS MOVE ID UNSELECT CLIENTACCESSRULES CLIENTNETWORKPRESENCELOCATION BACKENDAUTHENTICATE CHILDREN IDLE NAMESPACE LITERAL+
    3 OK CAPABILITY completed.
    �y�xm��4 NAMESPACE
    4 BAD User is authenticated but not connected.
    �M�S

@ltjdym
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ltjdym commented Dec 21, 2017

----------IMAP----------

  • OK The Microsoft Exchange IMAP4 service is ready. [TQBXAEgAUABSADIAMgBDAEEAMAAwADEANwAuAG4AYQBtAHAAcgBkADIAMgAuAHAAcgBvAGQALgBvAHUAdABsAG8AbwBrAC4AYwBvAG0A]
    �oIY1 CAPABILITY
  • CAPABILITY IMAP4 IMAP4rev1 AUTH=PLAIN AUTH=XOAUTH2 SASL-IR UIDPLUS ID UNSELECT CHILDREN IDLE NAMESPACE LITERAL+
    1 OK CAPABILITY completed.
    2 LOGIN "xxxxx@xxxx.org" *********
    2 OK LOGIN completed.
    3 CAPABILITY
  • CAPABILITY IMAP4 IMAP4rev1 AUTH=PLAIN AUTH=XOAUTH2 SASL-IR UIDPLUS MOVE ID UNSELECT CLIENTACCESSRULES CLIENTNETWORKPRESENCELOCATION BACKENDAUTHENTICATE CHILDREN IDLE NAMESPACE LITERAL+
    3 OK CAPABILITY completed.
    �����4 NAMESPACE
    4 BAD User is authenticated but not connected.

�dY

@ltjdym
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ltjdym commented Dec 21, 2017

im unable to turn on IMAP in my outlook.com account. I think that's the culprit.

@InfopactMLoos
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This issue is closed and not being pursuit anymore, please open a new issue.

@thomaswieland
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Hey everyone, good news (or bad news, it depends :-)

I fixed the issue for me, and maybe that helps narrowing down the problem for others. I tried various things back and forth, and I set up a hMailServer just for debugging. And the magic bullet was to disable the "PLAIN" authentication, and use "LOGIN" only. So what I see is that if PLAIN is enabled, Mailspring will try to do PLAIN authentication and finally fail. Doesn´t matter what else is enabled, it will only try PLAIN when PLAIN is enabled. If PLAIN is disabled, it will try LOGIN, which works for me. At least I get beyond the initial setup dialog and can sync my emails.

Maybe someone can fix the code with this information?

Thanks, Thomas

@byteSamurai
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@thomaswieland I just tried to reproduce it using my own mail server. Do you use Linux? Because only in Linux (Fedora) I am able to reproduce it. In Windows everything works well.

@thomaswieland
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@fr3dm4n I am using Mailspring on Windows 7 Enterprise x64. As SMTP Server I failed to connect

  • Exchange Server 2013 (Windows) with NTLM authentication
  • Postfix (Unix) without authentication (Source IP whitelist)
  • and initially hMailServer (Windows) with PLAIN and LOGIN

hMailServer had PLAIN and LOGIN authentication enabled at first; I couldn´t set up Mailspring, I got stuck with the error messages (see above). After disabling PLAIN auth on hMailServer (offering only LOGIN auth), I could set up Mailspring successfully. Does that answer your question?

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