Connect with Pidgin to Lync 2013 in Linux Mint 17.3 (Ubuntu 14.04)

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Published on January 13th 2016 - Listed in Linux Windows


It took me quite a while but eventually I got it working: Using Pidgin on Linux Mint and connect it to the company's Lync 2013 server. I installed the following packages:

sudo apt-get install pidgin pidgin-sipe

Afterwards I needed to handle quite a few hickups.

Problem 1: Self-Signed certificates

The first problem was that the internal SIP server had self-signed certificates and Pidgin refused to connect to the server:

(10:24:14) proxy: Connected to sipserver01:5061.
(10:24:14) nss: subject=CN=sipserver01.company.local,OU=IT,O=Company,L=Zuerich,ST=Zuerich,C=CH issuer=CN=Company CA,O=Company,C=CH
(10:24:14) nss: partial certificate chain
(10:24:14) certificate/x509/tls_cached: Starting verify for sipserver01
(10:24:14) certificate/x509/tls_cached: Checking for cached cert...
(10:24:14) certificate/x509/tls_cached: ...Not in cache
(10:24:14) nss: CERT 0. CN=sipserver01.nzzmg.local,OU=IT,O=Company,L=Zuerich,ST=Zuerich,C=CH :
(10:24:14) nss:   ERROR -8179: SEC_ERROR_UNKNOWN_ISSUER
(10:24:14) certificate: Failed to verify certificate for poolzh01
(10:24:14) connection: Connection error on 0x7fc15343b8f0 (reason: 0 description: SSL peer presented an invalid certificate)

Although there are a lot of pidgin bugs/requests open to allow self-signed certificates, there is a manual workaround. I downloaded the SSL certificate by using the following openssl command:

openssl s_client -connect sip.company.local:443

This gave me the output of the server's first certificate and the information with which certificate it was signed. This turned out to be another self-signed CA certificate which was deployed on all Windows workstations.
In order to get the CA certificate I went into a Windows machine running in the company's domain, I did the following steps:

Open Internet Explorer -> Internet Options -> Content (Inhalte in German) -> Certificates -> Intermediate Certification Authorities (Zwischenzertifizierungsstellen)

In my case, the company's CA certificate could be selected in this list and I exported it as Base-64 coded X509 certificate.

Now that I got both certificates (the main server certificate plus it's issuing certificate), I saved them in the following paths:

  • ~/.purple/certificates/x509/tls_cached/
  • ~/.purple/certificates/x509/tls_peers/

 However this was still not sufficiant because Pidgin reported that the Company CA certificate was not trusted. So I needed to copy the CA certificate into /etc/ssl/certs, too. After this, first success:

(10:39:13) certificate/x509/ca: Lazy init completed.
(10:39:13) nss/x509: Exporting certificate to /home/admck/.purple/certificates/x509/tls_peers/sipserver.company.local
(10:39:13) util: Writing file /home/admck/.purple/certificates/x509/tls_peers/sipserver.company.local
(10:39:13) nss: Trusting CN=sipserver01.company.local,OU=IT,O=Company,L=Zuerich,ST=Zuerich,C=CH
(10:39:13) certificate: Successfully verified certificate for sipserver.company.local
(10:39:13) stun: using server

Problem 2: Authentication problems - update pidgin-sipe plugin

I found a lot of pages describing different Pidgin settings to connect to Lync, here are some:

I tried all kinds of combination using NTLM, Auto, TLS authentication, etc. I got a "401 - Unauthorized: Access is denied due to invalid credentials", later a "certificate request failed", depending on the settings.

Eventually I decided to try the newest piding-sipe plugin (as of this writing 1.20). Unfortunately in Linux Mint 13.7 (and therefore Ubuntu 14.04 trusty), the package version is at 1.17. I decided to add a PPA repository which contained the new version:

sudo add-apt-repository ppa:sipe-collab/ppa
You are about to add the following PPA to your system:
 More info: https://launchpad.net/~sipe-collab/+archive/ubuntu/ppa
Press [ENTER] to continue or ctrl-c to cancel adding it

Executing: gpg --ignore-time-conflict --no-options --no-default-keyring --homedir /tmp/tmp.LiRa3uJQ8z --no-auto-check-trustdb --trust-model always --keyring /etc/apt/trusted.gpg --primary-keyring /etc/apt/trusted.gpg --keyserver hkp://keyserver.ubuntu.com:80 --recv-keys F93FF666
gpg: requesting key F93FF666 from hkp server keyserver.ubuntu.com
gpg: key F93FF666: public key "Launchpad PPA for Sipe plugin collaboration" imported
gpg: Total number processed: 1
gpg:               imported: 1  (RSA: 1)

And then installed the new version:

sudo apt-get install pidgin-sipe
[...]
The following packages will be upgraded:
  libnice10 libpurple0 pidgin pidgin-data pidgin-sipe
[...]

Besides showing more details in the debug log, the new pidgin-sipe version also offered an additional authentication mechanism (but it's not needed in this case).

Solving it: Using the correct settings

Although I updated pidgin-sipe to the newest version, the same errors still appeared: "sipe certificate request CertProvisioningService.svc failed" and other failures with "Webticket failed". Finally I got it working with the follwing account settings:

[ Basic ]

Protocol: Office Communicator
Username: myemail@company.local
Login: Empty
Password: mypassword
Local alias: Empty

[ Advanced ]

Server[:Port]: Empty
Connection type: Auto
User Agent: UCCAPI/4.0.7577.0 OC/4.0.7577.0 (Microsoft Lync 2010)
Authentication scheme: Auto
Use Single Sign-On: Not checked

The fact that server/port is left empty requires a correct DNS setup for your domaine. Check out https://technet.microsoft.com/en-us/library/gg398758%28v=ocs.15%29.aspx for more information.

Interestingly, the User Agent seems to be very important for the connection.

Pidgin connect to Lync server

With these settings I was finally able to connect to the Lync server with Pidgin!


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Comments (newest first)

Claudio Kuenzler from Switzerland wrote on Jul 13th, 2016:

Unfortunately only IM. But I'm not sure whether this is a Pidgin or a Lync connection problem.


Patrick Rynhart from New Zealand wrote on Jul 13th, 2016:

Awesome! Are you able to do Voice Calls ? Or IM only ? Thanks, Patrick