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help with tls config in stunnel
by Daniel Trickett 10 May '18

10 May '18

Hi, We are running stunnel 5.44 on Solaris. Our b2b legacy system is using TLS 1.0. We have a supplier who recently switched to TLS 1.2 and we can no longer connect to the site from our b2b. How can I configure stunnel to connect to the supplier site using TLS 1.2? TIA. Dan T This message and any attachment are confidential and may be privileged or otherwise protected from disclosure. If you are not the intended recipient, you must not copy this message or attachment or disclose the contents to any other person. If you have received this transmission in error, please notify the sender immediately and delete the message and any attachment from your system. Merck KGaA, Darmstadt, Germany and any of its subsidiaries do not accept liability for any omissions or errors in this message which may arise as a result of E-Mail-transmission or for damages resulting from any unauthorized changes of the content of this message and any attachment thereto. Merck KGaA, Darmstadt, Germany and any of its subsidiaries do not guarantee that this message is free of viruses and does not accept liability for any damages caused by any virus transmitted therewith. Click http://www.emdgroup.com/emd/imprint/mail_disclaimer.html to access the German, French, Spanish and Portuguese versions of this disclaimer.

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How to tell if commuications are encrypted?
by Alex Birchall 10 May '18

10 May '18

Hello, I have Stunnel installed on Windows Server 2008 R2, running as a service. I have it installed as a client on a Windows POS 2009 device. This setup is working, in that the client is operating correctly and using Stunnel. But how can I tell if communications between the Stunnel client and the Stunnel server are being encrypted, rather than Stunnel just doing port forwarding? I did read the client needs to have access to the server's certificate, but at the moment it does not. Alex

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Stunnel to Outlook
by DPS Support 09 May '18

09 May '18

I am trying to get a device on my network to send pop email notifications to my outlook account but can't seem to get it to work. I have enabled the outlook account to accept pop and enabled the client to send them. I'm not sure if I'm missing something or what, any help would be greatly appreciated. Here is my config: debug = info output = stunnel.log [outlook-pop3] client = yes accept = 110 connect = pop-mail.outlook.com:995 [outlook-imap] client = yes accept = 143 connect = imap-mail.outlook.com:993 [outlook-smtp] protocol = smtp client = yes accept = 25 connect = smtp-mail.outlook.com:587 Here is the log as well: 2018.05.08 15:15:03 LOG5[main]: stunnel 5.44 on x86-pc-msvc-1500 platform 2018.05.08 15:15:03 LOG5[main]: Compiled/running with OpenSSL 1.0.2m-fips 2 Nov 2017 2018.05.08 15:15:03 LOG5[main]: Threading:WIN32 Sockets:SELECT,IPv6 TLS:ENGINE,FIPS,OCSP,PSK,SNI 2018.05.08 15:15:03 LOG5[main]: Reading configuration from file stunnel.conf 2018.05.08 15:15:03 LOG5[main]: UTF-8 byte order mark detected 2018.05.08 15:15:03 LOG5[main]: FIPS mode disabled 2018.05.08 15:15:03 LOG6[main]: Initializing service [outlook-pop3] 2018.05.08 15:15:03 LOG4[main]: Service [outlook-pop3] needs authentication to prevent MITM attacks 2018.05.08 15:15:03 LOG6[main]: Initializing service [outlook-imap] 2018.05.08 15:15:03 LOG4[main]: Service [outlook-imap] needs authentication to prevent MITM attacks 2018.05.08 15:15:03 LOG6[main]: Initializing service [outlook-smtp] 2018.05.08 15:15:03 LOG4[main]: Service [outlook-smtp] needs authentication to prevent MITM attacks 2018.05.08 15:15:03 LOG5[main]: Configuration successful 2018.05.08 15:15:03 LOG5[main]: Logging to C:\Users\dps_engineer\AppData\Local\stunnel.log 2018.05.08 15:15:53 LOG5[0]: Service [outlook-pop3] accepted connection from 126.10.230.254:52629 2018.05.08 15:15:53 LOG6[0]: failover: round-robin, starting at entry #1 2018.05.08 15:15:53 LOG6[0]: s_connect: connecting 40.97.135.130:995 2018.05.08 15:15:53 LOG5[0]: s_connect: connected 40.97.135.130:995 2018.05.08 15:15:53 LOG5[0]: Service [outlook-pop3] connected remote server from 126.10.218.222:60145 2018.05.08 15:15:53 LOG6[0]: SNI: sending servername: pop-mail.outlook.com 2018.05.08 15:15:53 LOG6[0]: Peer certificate not required 2018.05.08 15:15:54 LOG6[0]: Certificate verification disabled 2018.05.08 15:15:54 LOG6[0]: Certificate verification disabled 2018.05.08 15:15:54 LOG6[0]: Client certificate not requested 2018.05.08 15:15:54 LOG6[0]: TLS connected: new session negotiated 2018.05.08 15:15:54 LOG6[0]: Negotiated TLSv1.2 ciphersuite ECDHE-RSA-AES256-GCM-SHA384 (256-bit encryption) 2018.05.08 15:15:55 LOG6[0]: Read socket closed (readsocket) 2018.05.08 15:15:55 LOG6[0]: SSL_shutdown successfully sent close_notify alert 2018.05.08 15:15:55 LOG6[0]: TLS socket closed (SSL_read) 2018.05.08 15:15:55 LOG5[0]: Connection closed: 58 byte(s) sent to TLS, 253 byte(s) sent to socket 2018.05.08 15:15:55 LOG5[1]: Service [outlook-smtp] accepted connection from 126.10.230.254:52639 2018.05.08 15:15:55 LOG6[1]: failover: round-robin, starting at entry #2 2018.05.08 15:15:55 LOG6[1]: s_connect: connecting 40.97.162.162:587 2018.05.08 15:15:55 LOG5[1]: s_connect: connected 40.97.162.162:587 2018.05.08 15:15:55 LOG5[1]: Service [outlook-smtp] connected remote server from 126.10.218.222:60147 2018.05.08 15:15:55 LOG6[1]: SNI: sending servername: smtp-mail.outlook.com 2018.05.08 15:15:55 LOG6[1]: Peer certificate not required 2018.05.08 15:15:55 LOG6[1]: Certificate verification disabled 2018.05.08 15:15:55 LOG6[1]: Certificate verification disabled 2018.05.08 15:15:55 LOG6[1]: Empty client CA list 2018.05.08 15:15:55 LOG6[1]: TLS connected: new session negotiated 2018.05.08 15:15:55 LOG6[1]: Negotiated TLSv1.2 ciphersuite ECDHE-RSA-AES256-GCM-SHA384 (256-bit encryption) 2018.05.08 15:16:00 LOG6[1]: TLS socket closed (SSL_read) 2018.05.08 15:16:00 LOG5[1]: Connection closed: 50 byte(s) sent to TLS, 194 byte(s) sent to socket 2018.05.08 15:16:00 LOG5[2]: Service [outlook-pop3] accepted connection from 126.10.230.254:52644 2018.05.08 15:16:00 LOG6[2]: failover: round-robin, starting at entry #2 2018.05.08 15:16:00 LOG6[2]: s_connect: connecting 40.97.161.50:995 2018.05.08 15:16:00 LOG5[2]: s_connect: connected 40.97.161.50:995 2018.05.08 15:16:00 LOG5[2]: Service [outlook-pop3] connected remote server from 126.10.218.222:60149 2018.05.08 15:16:00 LOG6[2]: SNI: sending servername: pop-mail.outlook.com 2018.05.08 15:16:00 LOG6[2]: Peer certificate not required 2018.05.08 15:16:00 LOG6[2]: Certificate verification disabled 2018.05.08 15:16:00 LOG6[2]: Certificate verification disabled 2018.05.08 15:16:00 LOG6[2]: Client certificate not requested 2018.05.08 15:16:00 LOG6[2]: TLS connected: new session negotiated 2018.05.08 15:16:00 LOG6[2]: Negotiated TLSv1.2 ciphersuite ECDHE-RSA-AES256-GCM-SHA384 (256-bit encryption) 2018.05.08 15:16:01 LOG6[2]: TLS socket closed (SSL_read) 2018.05.08 15:16:01 LOG5[2]: Connection closed: 58 byte(s) sent to TLS, 253 byte(s) sent to socket 2018.05.08 15:16:01 LOG5[3]: Service [outlook-smtp] accepted connection from 126.10.230.254:52647 2018.05.08 15:16:01 LOG6[3]: failover: round-robin, starting at entry #3 2018.05.08 15:16:01 LOG6[3]: s_connect: connecting 40.97.162.146:587 2018.05.08 15:16:01 LOG5[3]: s_connect: connected 40.97.162.146:587 2018.05.08 15:16:01 LOG5[3]: Service [outlook-smtp] connected remote server from 126.10.218.222:60150 2018.05.08 15:16:01 LOG6[3]: SNI: sending servername: smtp-mail.outlook.com 2018.05.08 15:16:01 LOG6[3]: Peer certificate not required 2018.05.08 15:16:01 LOG6[3]: Certificate verification disabled 2018.05.08 15:16:01 LOG6[3]: Certificate verification disabled 2018.05.08 15:16:01 LOG6[3]: Empty client CA list 2018.05.08 15:16:01 LOG6[3]: TLS connected: new session negotiated 2018.05.08 15:16:01 LOG6[3]: Negotiated TLSv1.2 ciphersuite ECDHE-RSA-AES256-GCM-SHA384 (256-bit encryption) 2018.05.08 15:16:03 LOG6[cron]: Executing cron jobs 2018.05.08 15:16:03 LOG6[cron]: Cron jobs completed in 0 seconds 2018.05.08 15:16:06 LOG6[3]: TLS socket closed (SSL_read) 2018.05.08 15:16:06 LOG5[3]: Connection closed: 50 byte(s) sent to TLS, 194 byte(s) sent to socket 2018.05.08 15:16:06 LOG5[4]: Service [outlook-pop3] accepted connection from 126.10.230.254:52653 2018.05.08 15:16:06 LOG6[4]: failover: round-robin, starting at entry #3 2018.05.08 15:16:06 LOG6[4]: s_connect: connecting 40.97.134.18:995 2018.05.08 15:16:06 LOG5[4]: s_connect: connected 40.97.134.18:995 2018.05.08 15:16:06 LOG5[4]: Service [outlook-pop3] connected remote server from 126.10.218.222:60153 2018.05.08 15:16:06 LOG6[4]: SNI: sending servername: pop-mail.outlook.com 2018.05.08 15:16:06 LOG6[4]: Peer certificate not required 2018.05.08 15:16:06 LOG6[4]: Certificate verification disabled 2018.05.08 15:16:06 LOG6[4]: Certificate verification disabled 2018.05.08 15:16:06 LOG6[4]: Client certificate not requested 2018.05.08 15:16:06 LOG6[4]: TLS connected: new session negotiated 2018.05.08 15:16:06 LOG6[4]: Negotiated TLSv1.2 ciphersuite ECDHE-RSA-AES256-GCM-SHA384 (256-bit encryption) 2018.05.08 15:16:07 LOG6[4]: Read socket closed (readsocket) 2018.05.08 15:16:07 LOG6[4]: SSL_shutdown successfully sent close_notify alert 2018.05.08 15:16:07 LOG6[4]: TLS socket closed (SSL_read) 2018.05.08 15:16:07 LOG5[4]: Connection closed: 58 byte(s) sent to TLS, 253 byte(s) sent to socket 2018.05.08 15:16:07 LOG5[5]: Service [outlook-smtp] accepted connection from 126.10.230.254:52656 2018.05.08 15:16:07 LOG6[5]: failover: round-robin, starting at entry #4 2018.05.08 15:16:07 LOG6[5]: s_connect: connecting 2603:1036:101::2:587 2018.05.08 15:16:07 LOG3[5]: s_connect: connect 2603:1036:101::2:587: Network is unreachable (WSAENETUNREACH) (10051) 2018.05.08 15:16:07 LOG6[5]: s_connect: connecting 2603:1036:102:108::2:587 2018.05.08 15:16:07 LOG3[5]: s_connect: connect 2603:1036:102:108::2:587: Network is unreachable (WSAENETUNREACH) (10051) 2018.05.08 15:16:07 LOG6[5]: s_connect: connecting 2603:1036:102:cc::2:587 2018.05.08 15:16:07 LOG3[5]: s_connect: connect 2603:1036:102:cc::2:587: Network is unreachable (WSAENETUNREACH) (10051) 2018.05.08 15:16:07 LOG6[5]: s_connect: connecting 2603:1036:102:8f::2:587 2018.05.08 15:16:07 LOG3[5]: s_connect: connect 2603:1036:102:8f::2:587: Network is unreachable (WSAENETUNREACH) (10051) 2018.05.08 15:16:07 LOG6[5]: s_connect: connecting 40.97.161.50:587 2018.05.08 15:16:08 LOG5[5]: s_connect: connected 40.97.161.50:587 2018.05.08 15:16:08 LOG5[5]: Service [outlook-smtp] connected remote server from 126.10.218.222:60158 2018.05.08 15:16:08 LOG6[5]: SNI: sending servername: smtp-mail.outlook.com 2018.05.08 15:16:08 LOG6[5]: Peer certificate not required 2018.05.08 15:16:08 LOG6[5]: Certificate verification disabled 2018.05.08 15:16:08 LOG6[5]: Certificate verification disabled 2018.05.08 15:16:08 LOG6[5]: Empty client CA list 2018.05.08 15:16:08 LOG6[5]: TLS connected: new session negotiated 2018.05.08 15:16:08 LOG6[5]: Negotiated TLSv1.2 ciphersuite ECDHE-RSA-AES256-GCM-SHA384 (256-bit encryption) 2018.05.08 15:16:13 LOG6[5]: TLS socket closed (SSL_read) 2018.05.08 15:16:13 LOG5[5]: Connection closed: 50 byte(s) sent to TLS, 194 byte(s) sent to socket Sent from Outlook<http://aka.ms/weboutlook>

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Stunnel Time out Error
by Sedick Cloete 07 May '18

07 May '18

HI All, We recently moved our email server from an in-house server to Office 365. We are now in the process of replacing all our XP boxes with Windows 10. One of the boxes are running the email service which collects emails from Office 365, that we have just recently upgraded. This process works on the XP but times out on windows 10. Attached, is the time out the log file. Below is the code I am using: Basic program code * variables ChannelNo = 0 Pop3Server = 'outlook.office365.com' Pop3User = UserName Pop3Pass = Password Pop3Port = '995' ProxYServer = '127.0.0.1' ProxyPort = '110' ProxyDir = 'C:\see4OI\SSL\' ProxyExe = 'stunnel.exe' ProxyCert = 'stunnel.pem' * retreives mail in MIME format Gosub GET_EMAILS return Mail_Rec * ---------------------------------------------------------------------------- ------------- GET_EMAILS: * close previous session If it wasnt closed properly Code = seeClose(ChannelNo) Code = seeRelease() * attach key code Code = seeAttach(1, KeyCode) if Code < 0 then RetFlag = 1 return end * start stunnel Code = seeSetProxySSL(0, 1, ProxyDir, ProxyCert, ProxyExe) If Code < 0 Then RETURN end * connect to email server Code = seePop3ConnectSSL(ChannelNo, ProxyPort, Pop3Port, Pop3Server, Pop3User, Pop3Pass, ProxyServer) If Code < 0 Then RETURN End Your assistance in this regard will be highly appreciated. Thank you. Kind Regards, Logicore SEDICK CLOETE IT Business Consultant Cell: 083 228 7058 Fax: 086 515 9695 email: sedick(a)logicore.co.za If you are not the intended recipient of this communication, please notify the sender immediately. The information and/or attachment contained in this email is confidential and may contain proprietary and/or personal information. It is meant solely for the intended recipient. Access to this email by anyone else is unauthorised. If you are not the intended recipient, any processing of the email or the information contained therein (including disclosure, copying, distribution, storage) or any action taken or omitted in reliance on this, is prohibited and may be unlawful.

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How to configure stunnel client on Mac
by Mark Foley 04 May '18

04 May '18

I've successfully set up stunnel for Windows and Linux clients. Now to set up for Mac. I've gone to the website http://macappstore.org/stunnel/ and followed the instructions there which are: 1. Press Command+Space and type Terminal and press enter/return key. 2. Run in Terminal app: ruby -e "$(curl -fsSL https://raw.githubusercontent.com/Homebrew/install/master/install)" < /dev/null 2> /dev/null and press enter/return key. 3. Run: brew install stunnel And then it says, "Done! You can now use stunnel." Well, not exactly. Where do I put my stunnel.conf and certificate.pem? How do I make stunnel run automatically at boot time? The web instructions aren't very complete. Need additional assistance. THX --Mark

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Stunnel in Windows Failover cluster
by Tobias Gillstöm 27 Apr '18

27 Apr '18

Hi, I'm currently using stunnel in a windows fail over cluster: My problem is that when a fail over occurs stunnel switches too the other node and says that stunnel is running and everything is fine. But when I check the logs for stunnel and the program that uses stunnel, it does not appear to be running or sending any data. In the screenshot you can see my stunnel configuration, in the startup parameters section it says "-service -install" my question is if it shouldn't say "-service -start" instead, has anyone else encountered this problem? And if this is the problem why does the stunnel service install with these parameters?

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Ubuntu 16.04.4 LTS SSLv3 and SSlv2 running stunnel 5.44
by Joe Phillips 25 Apr '18

25 Apr '18

I am running stunnel 5.44 on Ubuntu 16.04.4 LTS with all updates. I cannot get devices to connect using sslv2 or 3. My conf file Options line as seen below : ;Enable support for inecure SSLv3 protocol Options = -NO_SSLv3 Options = -NO_SSLv2 I continuously get error 1408A10B SSL routines: ssl3_get_client_hello:wrong version number Do I not have SSL3 and 2 correctly defined in my conf file? I realize 2 and 3 are no longer secure, but I need to support them while I transition to TLS 1.2 thanks [cid:image001.png@01D3DC17.D1AFBC30]

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stunnel as a Windows Service
by Paul Muller 20 Apr '18

20 Apr '18

Does anyone have any documentation on how to setup stunnel as a Windows Service? I currently have it installed on a Windows Server 2012 R2 Standard. I noticed that stunnel stops running as soon as I log off of my RDP session on the server. [logo1] Paul A. Muller * Systems and Networking Consultant Earnest & Associates * Profitability Improvement Specialists Voice: 305.822.5353 x354 * Fax: 305.822.5848 Email: paul.muller(a)earnestassoc.com<mailto:paul.muller@earnestassoc.com> * Web: earnestassoc.com<http://www.earnestassoc.com/> * Twitter: @earnestassoc<http://twitter.com/earnestassoc>

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Rapid subsequent DNS resolution fails within stunnel
by Vincent Deschenes 20 Apr '18

20 Apr '18

Hi, We have had this weird problem for a long time where sometime DNS resolution will fail with this error: Error resolving 'domain name printed here': Neither nodename nor servname known (EAI_NONAME) Today I found out that this will happen when stunnel get 2 calls for the same outgoing endpoint very fast one after the other. One call will work no problem. But if you do 2 one after the other then the second one and all other subsequent will fail. Wait a bit and try again, the first one will pass and then others will fail. DNS resolution on the server (linux) itself work without problem, nslookup in loops no problem. But with stunnel we always have the problem. The only working solution is to add a record to the server host file. Any idea ? Could this be a bug in stunnel ? Thanks, Vincent

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Authentication
by Paul Muller 20 Apr '18

20 Apr '18

When I first setup stunnel, I changed my software to reflect the [gmail-smtp] entries in my configuration file. When I tried to send an email from my application I received the following message: "No Email sent, Error 535-5.7.8 Username and Password not accepted." Then I remarked out the authentication credentials in my software. When I tried to send an email I received the following message: "No Email sent, Error-5.5.1 Authentication Required." My question is, can place my authentication credentials in the "stunnel.conf" file? And if so, where? Thanks, [logo1] Paul A. Muller * Systems and Networking Consultant Earnest & Associates * Profitability Improvement Specialists Voice: 305.822.5353 x354 * Fax: 305.822.5848 Email: paul.muller(a)earnestassoc.com<mailto:paul.muller@earnestassoc.com> * Web: earnestassoc.com<http://www.earnestassoc.com/> * Twitter: @earnestassoc<http://twitter.com/earnestassoc>

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