Unknown mailsmtp error 27 (SSL Error) when adding IMAP/SMTP account

[stefvonb]

Are there any related issues?

Similar, but not the same

What operating system are you using?

Ubuntu 16.04 LTS

What version of Mailspring are you using?

1.0.8

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.)?

No

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

I'm running into trouble setting up a simple IMAP/SMTP account. I managed to do this on Nylas with no issues (and on countless other mail programs). Note that this is on the same computer Nylas was installed on, but I have since removed it.

The IMAP seems to connect easily, but SMTP crashes with a pretty bland error message. This is from the suggested log file:

----------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 svonbudd *********
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) "/" Archive
* LIST (\HasNoChildren) "/" Calendar
* LIST (\HasNoChildren) "/" Contacts
* LIST (\HasNoChildren) "/" "Deleted Items"
* LIST (\HasNoChildren) "/" "Deleted Messages"
* LIST (\HasNoChildren) "/" Drafts
* LIST (\Marked \HasNoChildren) "/" INBOX
* LIST (\HasNoChildren) "/" Journal
* LIST (\HasNoChildren) "/" Junk
* LIST (\HasNoChildren) "/" "Junk E-Mail"
* LIST (\HasNoChildren) "/" N1-Snoozed
* LIST (\HasNoChildren) "/" Notes
* LIST (\HasNoChildren) "/" Outbox
* LIST (\HasNoChildren) "/" Sent
* LIST (\HasNoChildren) "/" "Sent Items"
* LIST (\HasNoChildren) "/" "Sent Messages"
* LIST (\HasNoChildren) "/" Tasks
* LIST (\HasNoChildren) "/" Trash
5 OK LIST completed.

----------SMTP----------

mailsmtp Last Error Code: 27

mailsmtp Last Error Location: 5

I could probably provide more info if I know what the SMTP errors are.

[RicardoEPRodrigues]

I have the same issue!

It's still active on 1.0.9.

[earandap]

I got it too on 1.0.10

[lourencoj]

Same problem here.

[bengotow]

Hey folks! Those errors are a bit cryptic, but map to a look up table here: https://github.com/dinhviethoa/libetpan/blob/master/src/low-level/smtp/mailsmtp_types.h#L75. It looks like 27 is the last one (SSL Error).

We have really strict SSL and security checking on by default in Mailspring and it doesn't turn it off unless you choose "Allow Insecure SSL" during IMAP/SMTP auth. It could be that your SMTP server has an invalid / self-signed SSL certificate, or the certificate expired or it's signed with a root cert that your machine doesn't trust. We also had some early problems with Mailspring not being able to find your computer's certificate trust chain on some distributions of Linux, so it may be that as well - let me know if you're running Linux!

[xulongwu4]

I am running linux and having this problem with 1.0.9.

[stefvonb]

Hi @bengotow

Thanks for the link! I am running Linux, using Ubuntu 16.04 LTS

[RicardoEPRodrigues]

I also tested this on Windows and it is still happening for me, even with Allow Insecure SSL.

[earandap]

Hi @bengotow

I am running Linux, using Ubuntu 17.10. I checked Allow Insecure SSL and the error changed.

EHLO ed-precision
250-******************************
250-SIZE 52428800
250-PIPELINING
250-DSN
250-ENHANCEDSTATUSCODES
250-STARTTLS
250-AUTH GSSAPI NTLM LOGIN
250-8BITMIME
250-BINARYMIME
250 CHUNKING
STARTTLS
ecision
220 2.0.0 SMTP server ready
4SEHLO ed-precision
250-*******************
250-SIZE 52428800
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: *********
SIZE 52428800
PIPELINING
DSN
ENHANCEDSTATUSCODES
AUTH GSSAPI NTLM LOGIN
8BITMIME
BINARYMIME
CHUNKING


mailsmtp Last Error Code: 17

mailsmtp Last Error Location: 10

[pablodecm]

Same problem both for Mac (High Sierra) and Linux (Ubuntu 16.04 LTS) client with 1.0.10, tested with and without Allow Insecure SSL.

[tobgaer]

Same problem, but only on Linux (Debian). On Windows 10 everything works fine. SMTP-Server is smtp.strato.de

[en4ble]

I have the same problem on Arch Linux, using client with 1.0.12, tested with and without Allow insecure SSL

[joshjabs]

Same here on Windows 10. Mail server has a self-signed cert and Mailspring won't let me connect regardless of whether 'Allow Insecure SSL' is checked or not.

[bburt33-zz]

Same problem here. macOS 10.13.2. Mailiwise 1.0.12. Tried all ports with and without Allow insecure SSL. Same settings are fine in other clients.