stunnel-users

2 participants
3307 discussions

Stunnel New User
by David Aitchison 07 Jan '09

07 Jan '09

Hello, I have a potential use for Stunnel on a project I am working on. Excuse the perhaps very silly questions, this is all new to me. I have read through the manual, and understand that Stunnel can either be run from the command line ad-hoc or as an application using the stunnel.conf configuration file. If I have Stunnel running on the server, does this mean that all mails that leave that server will be SSL encrypted? I have a requirement to send mails out over SSL, but my application doesn't support that, it does support sending out over standard SMTP port 25, but I need it to use port 465? Thanks in advance, David Aitchison

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Re: [stunnel-users] Problem with the client certificate
by Michael Renner 03 Jan '09

03 Jan '09

On Thursday 01 January 2009, Christophe Nanteuil wrote: > Well, > I think the problem comes from the CAfile, ie the cert used to verify the > other certs. This is right. I thought that the CA file is not essential with verify depths less than 2. It seems this was a mistake. This time (yes, I use tinyCA), I made and used client- and server certificates as well as the CA. Now it works. Thanks for your help! > To test, I think it is better to have only one section per file : > - your key (section ----BEGIN RSA PRIVATE KEY----- to ---END RSA...) in the > key file corresponding to key=file in config file. > - your certificate (section ----BEGIN CERTIFICATE ----- to ---END > CERTIFICATE...) in the cert file corresponding to cert=file in the config > file. > These files must exist for server and client since you want mutual > authentication. > For verifying the certificate, you need to put the client certificate > (autosigned) in the CAfile option of the server config file. > The same for the client : put the server certificate in the CAfile option > of the client config file. > > on the server, the command 'openssl verify -CAfile client_cert.pem > client_cert.pem' should return ok > on the client, the command 'openssl verify -CAfile server_cert.pem > server_cert.pem' should return ok. > It can seem stupid but, as you have self-signed certificate, the CAfile is > the cert file. > > If you use tinyCA, you can easily build your own CA with one CA cert and > several certs for clients or servers. Then, you would be able to have the > same CAfile on the client and on the server. > > I hope this is clear enough. If not, write me back. > > > > > 2008/12/31 Michael Renner <michael.renner(a)gmx.de> > > > On Tuesday 30 December 2008, you wrote: > > > Hello, > > > > Happy new year! > > > > > * are the permissions correct on your files : > > > - key must belong to the user and have 0600 status (read only by the > > > > user) > > > > > - cert must belong to the user. > > > > I think the permissions are OK. The file is owed by root and loaded at > > the start > > Wrote 1024 new random bytes to /root/.rnd > > RAND_status claims sufficient entropy for the PRNG > > PRNG seeded successfully > > Certificate: /etc/stunnel/stunnelclient.pem > > Certificate loaded > > Key file: /etc/stunnel/stunnelclient.pem > > Private key loaded > > SSL context initialized for service BreakOut > > > > > * Is the content of the cert file of this form > > > > > > -----BEGIN CERTIFICATE----- > > > certificate data here > > > -----END CERTIFICATE----- > > > ? > > > and the content of the key file this form > > > -----BEGIN RSA PRIVATE KEY----- > > > key datat here > > > -----END RSA PRIVATE KEY----- > > > > I made several files. According to > > http://www.stunnel.org/faq/certs.html#ToC5 > > I got a file with a certificate, a RSA Key and a DH section (I removed > > the password for the certificate). > > > > According to http://www.stunnel.org/examples/client_cert.html I got a > > different file: it has a certificate and a RSA section and between them > > an other section: > > > > rcnyy/AbS1YPkdggJSnw+fqzg/L/QvQB6GTT5KWJzd0= > > -----END RSA PRIVATE KEY----- > > Certificate: > > Data: > > Version: 3 (0x2) > > Serial Number: 5 (0x5) > > Signature Algorithm: sha1WithRSAEncryption > > Issuer: C=DE, ST=Germany, L=Munich, O=vbox4php, OU=Rektorat, > > CN=DE/emailAddress=michael.renner(a)gmx.de > > Validity > > Not Before: Dec 28 20:37:19 2008 GMT > > Not After : Dec 28 20:37:19 2009 GMT > > Subject: C=DE, ST=Germany, O=vbox4php, OU=stunnel, > > CN=boulder.vbox4php.org/[email protected] > > Subject Public Key Info: > > Public Key Algorithm: rsaEncryption > > RSA Public Key: (1024 bit) > > Modulus (1024 bit): > > 00:b1:05:47:7a:27:4f:19:2b:18:72:e3:3c:f6:a6: > > . > > . > > 2b:55:2d:c9:dc:96:55:14:bb > > Exponent: 65537 (0x10001) > > X509v3 extensions: > > X509v3 Basic Constraints: > > CA:FALSE > > Netscape Cert Type: > > SSL Server > > Netscape Comment: > > TinyCA Generated Certificate > > X509v3 Subject Key Identifier: > > > > 86:F6:1F:71:29:AA:A5:61:DF:B2:81:F2:34:3A:A6:9E:58:C8:6A:5E X509v3 > > Authority Key Identifier: > > > > keyid:72:68:1A:0C:9D:E9:93:81:07:E9:36:71:75:33:05:C6:70:35:01:BF > > > > > > DirName:/C=DE/ST=Germany/L=Munich/O=vbox4php/OU=Rektorat/CN=DE/emailAddre > >ss= michael.renner(a)gmx.de > > serial:BC:97:82:4E:E3:9F:FE:5A > > > > X509v3 Issuer Alternative Name: > > email:[email protected] > > <email%3Amichael.renner(a)gmx.de> X509v3 Subject Alternative Name: > > email:[email protected] > > <email%3Amichael.renner(a)gmx.de> Signature Algorithm: > > sha1WithRSAEncryption > > 49:ef:06:aa:e5:71:b1:6e:23:87:02:9d:ce:56:e1:3b:77:5a: > > . > > . > > 41:93:92:ee:57:23:95:f3:99:62:27:6a:a4:b7:85:b4:92:86: > > 22:50:79:a0 > > -----BEGIN CERTIFICATE----- > > > > Anyhow: it fails: > > 2008.12.31 17:51:07 LOG4[13056:1073809760]: VERIFY ERROR: depth=0, > > error=unable to get local issuer > > certificate: /C=DE/ST=Germany/O=vbox4php/OU=stunnel/CN= > > boulder.vbox4php.org/[email protected] > > 2008.12.31 17:51:07 LOG3[13056:1073809760]: SSL_accept: 140890B2: > > error:140890B2:SSL routines:SSL3_GET_CLIENT_CERTIFICATE:no certificate > > returned > > > > With strace I can see the the key and the cert is OK on the client side: > > (I assume that it is only read once): > > > > [pid 11829] open("/etc/stunnel/stunnelserver.pem", O_RDONLY) = 4 > > [pid 11829] fstat(4, {st_mode=S_IFREG|0600, st_size=5521, ...}) = 0 > > [pid 11829] mmap(NULL, 4096, PROT_READ|PROT_WRITE, MAP_PRIVATE| > > MAP_ANONYMOUS, -1, 0) = 0x7f8f5f13b000 > > [pid 11829] read(4, "-----BEGIN RSA PRIVATE KEY-----\n"..., 4096) = 4096 > > [pid 11829] read(4, "VQQDEwJERTEkMCIGCSqGSIb3\nDQEJARY"..., 4096) = 1425 > > [pid 11829] read(4, "", 4096) = 0 > > [pid 11829] close(4) = 0 > > [pid 11829] munmap(0x7f8f5f13b000, 4096) = 0 > > [pid 11829] write(2, "2008.12.31 17:52:56 LOG7[11829:1"..., 682008.12.31 > > 17:52:56 LOG7[11829:140253752059616]: Certificate loaded > > ) = 68 > > [pid 11829] write(2, "2008.12.31 17:52:56 LOG7[11829:1"..., 902008.12.31 > > 17:52:56 LOG7[11829:140253752059616]: Key > > file: /etc/stunnel/stunnelserver.pem > > ) = 90 > > [pid 11829] open("/etc/stunnel/stunnelserver.pem", O_RDONLY) = 4 > > [pid 11829] fstat(4, {st_mode=S_IFREG|0600, st_size=5521, ...}) = 0 > > [pid 11829] mmap(NULL, 4096, PROT_READ|PROT_WRITE, MAP_PRIVATE| > > MAP_ANONYMOUS, -1, 0) = 0x7f8f5f13b000 > > [pid 11829] read(4, "-----BEGIN RSA PRIVATE KEY-----\n"..., 4096) = 4096 > > [pid 11829] close(4) = 0 > > [pid 11829] munmap(0x7f8f5f13b000, 4096) = 0 > > [pid 11829] write(2, "2008.12.31 17:52:56 LOG7[11829:1"..., 682008.12.31 > > 17:52:56 LOG7[11829:140253752059616]: Private key loaded > > > > > > While I see in the clients logfile: > > SSL state (connect): SSLv3 flush data > > SSL alert (read): fatal: bad certificate > > SSL_connect: 14094412: error:14094412:SSL routines:SSL3_READ_BYTES:sslv3 > > alert > > bad certificate > > Connection reset: 0 bytes sent to SSL, 0 bytes sent to socket > > > > > > Strange! > > > > > > One more hint? > > -- > > > > |Michael Renner E-mail: michael.renner(a)gmx.de | > > |D-81541 Munich Germany ICQ: #112280325 | > > |Germany Don't drink as root! ESC:wq -- |Michael Renner E-mail: michael.renner(a)gmx.de | |D-81541 Munich Germany ICQ: #112280325 | |Germany Don't drink as root! ESC:wq

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hiding a proxy that appear like a web server?
by Michael Renner 03 Jan '09

03 Jan '09

Moin, I want to use stunnel (in conjunction with prtunnel) to reach my own proxy server out of a restricted network. The normal stunnel connection works so far without a problem. But I am looking for a possibility that this connection (reaching the endpoint of stunnel with my proxy server behind) appears like a normal webserver (maybe with just one simple index.html) to others. Any ideas? Thanks -- |Michael Renner E-mail: michael.renner(a)gmx.de | |D-81541 Munich Germany ICQ: #112280325 | |Germany Don't drink as root! ESC:wq

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Re: [stunnel-users] Problem with the client certificate
by Michael Renner 31 Dec '08

31 Dec '08

On Tuesday 30 December 2008, you wrote: > Hello, Happy new year! > * are the permissions correct on your files : > - key must belong to the user and have 0600 status (read only by the user) > - cert must belong to the user. I think the permissions are OK. The file is owed by root and loaded at the start Wrote 1024 new random bytes to /root/.rnd RAND_status claims sufficient entropy for the PRNG PRNG seeded successfully Certificate: /etc/stunnel/stunnelclient.pem Certificate loaded Key file: /etc/stunnel/stunnelclient.pem Private key loaded SSL context initialized for service BreakOut > * Is the content of the cert file of this form > > -----BEGIN CERTIFICATE----- > certificate data here > -----END CERTIFICATE----- > ? > and the content of the key file this form > -----BEGIN RSA PRIVATE KEY----- > key datat here > -----END RSA PRIVATE KEY----- I made several files. According to http://www.stunnel.org/faq/certs.html#ToC5 I got a file with a certificate, a RSA Key and a DH section (I removed the password for the certificate). According to http://www.stunnel.org/examples/client_cert.html I got a different file: it has a certificate and a RSA section and between them an other section: rcnyy/AbS1YPkdggJSnw+fqzg/L/QvQB6GTT5KWJzd0= -----END RSA PRIVATE KEY----- Certificate: Data: Version: 3 (0x2) Serial Number: 5 (0x5) Signature Algorithm: sha1WithRSAEncryption Issuer: C=DE, ST=Germany, L=Munich, O=vbox4php, OU=Rektorat, CN=DE/emailAddress=michael.renner(a)gmx.de Validity Not Before: Dec 28 20:37:19 2008 GMT Not After : Dec 28 20:37:19 2009 GMT Subject: C=DE, ST=Germany, O=vbox4php, OU=stunnel, CN=boulder.vbox4php.org/[email protected] Subject Public Key Info: Public Key Algorithm: rsaEncryption RSA Public Key: (1024 bit) Modulus (1024 bit): 00:b1:05:47:7a:27:4f:19:2b:18:72:e3:3c:f6:a6: . . 2b:55:2d:c9:dc:96:55:14:bb Exponent: 65537 (0x10001) X509v3 extensions: X509v3 Basic Constraints: CA:FALSE Netscape Cert Type: SSL Server Netscape Comment: TinyCA Generated Certificate X509v3 Subject Key Identifier: 86:F6:1F:71:29:AA:A5:61:DF:B2:81:F2:34:3A:A6:9E:58:C8:6A:5E X509v3 Authority Key Identifier: keyid:72:68:1A:0C:9D:E9:93:81:07:E9:36:71:75:33:05:C6:70:35:01:BF DirName:/C=DE/ST=Germany/L=Munich/O=vbox4php/OU=Rektorat/CN=DE/[email protected] serial:BC:97:82:4E:E3:9F:FE:5A X509v3 Issuer Alternative Name: email:[email protected] X509v3 Subject Alternative Name: email:[email protected] Signature Algorithm: sha1WithRSAEncryption 49:ef:06:aa:e5:71:b1:6e:23:87:02:9d:ce:56:e1:3b:77:5a: . . 41:93:92:ee:57:23:95:f3:99:62:27:6a:a4:b7:85:b4:92:86: 22:50:79:a0 -----BEGIN CERTIFICATE----- Anyhow: it fails: 2008.12.31 17:51:07 LOG4[13056:1073809760]: VERIFY ERROR: depth=0, error=unable to get local issuer certificate: /C=DE/ST=Germany/O=vbox4php/OU=stunnel/CN=boulder.vbox4php.org/emailAddress=michael.renner(a)gmx.de 2008.12.31 17:51:07 LOG3[13056:1073809760]: SSL_accept: 140890B2: error:140890B2:SSL routines:SSL3_GET_CLIENT_CERTIFICATE:no certificate returned With strace I can see the the key and the cert is OK on the client side: (I assume that it is only read once): [pid 11829] open("/etc/stunnel/stunnelserver.pem", O_RDONLY) = 4 [pid 11829] fstat(4, {st_mode=S_IFREG|0600, st_size=5521, ...}) = 0 [pid 11829] mmap(NULL, 4096, PROT_READ|PROT_WRITE, MAP_PRIVATE| MAP_ANONYMOUS, -1, 0) = 0x7f8f5f13b000 [pid 11829] read(4, "-----BEGIN RSA PRIVATE KEY-----\n"..., 4096) = 4096 [pid 11829] read(4, "VQQDEwJERTEkMCIGCSqGSIb3\nDQEJARY"..., 4096) = 1425 [pid 11829] read(4, "", 4096) = 0 [pid 11829] close(4) = 0 [pid 11829] munmap(0x7f8f5f13b000, 4096) = 0 [pid 11829] write(2, "2008.12.31 17:52:56 LOG7[11829:1"..., 682008.12.31 17:52:56 LOG7[11829:140253752059616]: Certificate loaded ) = 68 [pid 11829] write(2, "2008.12.31 17:52:56 LOG7[11829:1"..., 902008.12.31 17:52:56 LOG7[11829:140253752059616]: Key file: /etc/stunnel/stunnelserver.pem ) = 90 [pid 11829] open("/etc/stunnel/stunnelserver.pem", O_RDONLY) = 4 [pid 11829] fstat(4, {st_mode=S_IFREG|0600, st_size=5521, ...}) = 0 [pid 11829] mmap(NULL, 4096, PROT_READ|PROT_WRITE, MAP_PRIVATE| MAP_ANONYMOUS, -1, 0) = 0x7f8f5f13b000 [pid 11829] read(4, "-----BEGIN RSA PRIVATE KEY-----\n"..., 4096) = 4096 [pid 11829] close(4) = 0 [pid 11829] munmap(0x7f8f5f13b000, 4096) = 0 [pid 11829] write(2, "2008.12.31 17:52:56 LOG7[11829:1"..., 682008.12.31 17:52:56 LOG7[11829:140253752059616]: Private key loaded While I see in the clients logfile: SSL state (connect): SSLv3 flush data SSL alert (read): fatal: bad certificate SSL_connect: 14094412: error:14094412:SSL routines:SSL3_READ_BYTES:sslv3 alert bad certificate Connection reset: 0 bytes sent to SSL, 0 bytes sent to socket Strange! One more hint? -- |Michael Renner E-mail: michael.renner(a)gmx.de | |D-81541 Munich Germany ICQ: #112280325 | |Germany Don't drink as root! ESC:wq

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Problem with the client certificate
by Michael Renner 27 Dec '08

27 Dec '08

Moin, it seems that I understood something wrong with stunnel client certificates. First of all: until now I run stunnel 4.18 and stunnel 4.21 with debian and kubuntu without client certificates (with success). I use it to reach a proprietary application through an untrusted network. Now, I want the clients to authenticate against the server. Therefor, as a quick and dirty test, I used the same stunnel.pem file at the server and at the client side. The configuration at the server side (where the application is waiting for connections, in this example it is just a script) looks like this: cert = /etc/stunnel/stunnel.pem #chroot = /var/run/stunnel/ pid = /tmp/stunnel.pid setuid = nobody setgid = nogroup output = /var/log/stunnel4.log exec = /root/stest.sh verify = 1 [BreakOut] accept = 192.168.0.1:443 Here is the configuration at the client side, where a browser establish a connection cert = /etc/stunnel/stunnel.pem key = /etc/stunnel/stunnel.pem sslVersion = SSLv3 chroot = /var/lib/stunnel4/ setuid = stunnel4 setgid = stunnel4 pid = /stunnel4.pid socket = l:TCP_NODELAY=1 socket = r:TCP_NODELAY=1 verify = 0 debug = 7 output = /var/log/stunnel4/stunnel.log client = yes [BreakOut] accept = 127.0.0.1:8080 connect = 192.168.0.1:443 First of all: is it right to set 'verify = 1' at the server side, and 'verify = 0' at the client side? It seems right to me, because the client should authenticate, but not the other way. Anyhow: As soon as a connection is opened using this configuration it will terminate at the same second. renner@mars:~$ telnet localhost 8080 Trying 127.0.0.1... Connected to localhost. Escape character is '^]'. Connection closed by foreign host. In the clients logfile I see SSL state (connect): before/connect initialization SSL state (connect): SSLv3 write client hello A SSL state (connect): SSLv3 read server hello A VERIFY IGNORE: depth=0, /C=DE/ST=Germany/L=Munich/O=vbox4php/OU=stunnel/CN=boulder.vbox4php.org/emailAddress=michael.renner(a)gmx.de VERIFY OK: depth=0, /C=DE/ST=Germany/L=Munich/O=vbox4php/OU=stunnel/CN=boulder.vbox4php.org/emailAddress=michael.renner(a)gmx.de VERIFY IGNORE: depth=0, /C=DE/ST=Germany/L=Munich/O=vbox4php/OU=stunnel/CN=boulder.vbox4php.org/emailAddress=michael.renner(a)gmx.de VERIFY OK: depth=0, /C=DE/ST=Germany/L=Munich/O=vbox4php/OU=stunnel/CN=boulder.vbox4php.org/emailAddress=michael.renner(a)gmx.de SSL state (connect): SSLv3 read server certificate A SSL state (connect): SSLv3 read server certificate request A SSL state (connect): SSLv3 read server done A SSL state (connect): SSLv3 write client certificate A SSL state (connect): SSLv3 write client key exchange A SSL state (connect): SSLv3 write certificate verify A SSL state (connect): SSLv3 write change cipher spec A SSL state (connect): SSLv3 write finished A SSL state (connect): SSLv3 flush data SSL alert (read): fatal: bad certificate SSL_connect: 14094412: error:14094412:SSL routines:SSL3_READ_BYTES:sslv3 alert bad certificate Connection reset: 0 bytes sent to SSL, 0 bytes sent to socket BreakOut finished (0 left) And, more interesting, at the server side: BreakOut connected from 84.57.55.105:57987 VERIFY ERROR: depth=0, error=self signed certificate: /C=DE/ST=Germany/L=Munich/O=vbox4php/OU=stunnel/CN=boulder.vbox4php.org/emailAddress=michael.renner(a)gmx.de SSL_accept: 140890B2: error:140890B2:SSL routines:SSL3_GET_CLIENT_CERTIFICATE:no certificate returned Connection reset: 0 bytes sent to SSL, 0 bytes sent to socket Is something wrong with my self signed certificate? In my first tests I used one that I made with tinyCA, an other was made according http://www.stunnel.org/faq/certs.html: * openssl req -new -x509 -days 365 -nodes -out stunnel.pem -keyout stunnel.pem * openssl gendh 512 >> stunnel.pem * openssl rsa -in stunnel.pem -out new.pem * edit new.pem, merge some parts with stunnel.pem and rename it Any hint? Thanks -- |Michael Renner E-mail: michael.renner(a)gmx.de | |D-81541 Munich Germany ICQ: #112280325 | |Germany Don't drink as root! ESC:wq

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Windows binary kits on 64 bit 2003 server or 2008 server
by Rich Jordan 24 Dec '08

24 Dec '08

Sorry to sully the list with wintel questions, but I haven't been able to locate an answer, and without systems available to test the obvious method of finding out is not available. We're running Stunnel V4.26 on a windows 2003 32-bit server, communicating with several better platforms running Stunnel V4.20 and newer, no issues. One interested customer is running windows 2003 server, 64-bit, and plans on moving to win2008 server 64 bit in the not too distant future. I do not have access to either OS/system and they're reluctant to install without knowing ahead of time what might happen. I'm hoping someone has tried the current STunnel binary kit on either or both of those systems. Will the kit run on 64-bit windows 2003, and is it usable on windows 2008? If not is this a situation where a build from source on either/both of those windows systems will produce working code? I've also found a number of hits for reputed OpenSSL ports for 64 bit windows. Any particular ones known to be good? Thanks for any info. Rich Illuc ivi, illud feci

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Re: [stunnel-users] Wrapping a CherryPy server?
by Lucas Burdick 19 Dec '08

19 Dec '08

Hmm, I guess I didn't send my previous followup to the list. After setting the log to output properly, I was able to troubleshoot my problem. The chroot directory was non-existent and therefore didn't allow my .pid to be created. I have created the directory and everything now works as it should. Thanks for the help. Sorry for the trouble. Lucas -----Original Message----- From: Michael Renner [mailto:[email protected]] Sent: December-19-08 11:07 AM To: stunnel-users(a)mirt.net; Lucas Burdick Subject: Re: [stunnel-users] Wrapping a CherryPy server? On Friday 19 December 2008, Lucas Burdick wrote: > Hi There, Moin, > I?m trying to encrypt a cherrypy web page that I?m serving up. The page > itself works just fine on port 80, but I can?t seem to get stunnel to wrap > it. I?m using 4.26 on CentOS 5.2. I?ve put in my stunnel.conf: [...] > I?ve also tried commenting out the above mentioned .conf entry. I get the > error that inetd mode needs a remote host or executable. I?m trying to run > in daemon mode but I don?t think I?m doing it right. > > Please help, or ask me questions, or tell me to elaborate or something. can you call stunnel using the forground option and check the logfile? start stunnel like this ... $ stunnel -D debug -f -o /var/log/stunnel.log ........ CU -- |Michael Renner E-mail: michael.renner(a)gmx.de | |D-81541 Munich Germany ICQ: #112280325 | |Germany Don't drink as root! ESC:wq

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Log rotation patch
by Christophe Nanteuil 17 Dec '08

17 Dec '08

Hello, NB : I propose this patch in alpha version. It has been tested only on a Linux Mandriva. (in the alpha version, it's recommended to use it on logs you might loose). Why to use this patch ? One reason I have to restart periodically stunnel is to do log rotation. This patch allows log rotation while running stunnel by implementing it directly inside. Therefore, the established connections are not closed by log rotation. Patch to version : 4.26 (should work on earlier versions). Type : new feature Description : Log rotation inside stunnel How to use this patch ? 3 new options are added in config file (see manual) maxLogSize : maximum size of log file (output option in config file). If logs have to be added, a log rotation is initiated. maxLogFiles : how many log files you want to keep. Default 7. useLogCompression : specify if rotated log files kept must be compressed or not. (requires zlib to be set). Just recompile stunnel after applying patch in stunnel directory: patch -p1 < /path/to/stunnel-logrot-0.10a.patch Test results are welcomed. Regards -- Christophe Nanteuil

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Re: [stunnel-users] Stunnel 4 failing to connect to gmail
by Alex Limberis 15 Dec '08

15 Dec '08

HI Asif, Unfortunately that is the way gmail works. It changes the from to the gmail address rather than the computer domain. Unfortunately, this mostly makes it useless if you are trying to use it as a smarthost. -----Original Message----- From: stunnel-users-bounces(a)mirt.net [mailto:[email protected]] On Behalf Of Asif Iqbal Sent: Monday, December 15, 2008 2:06 PM To: Scott Gifford Cc: stunnel-users(a)mirt.net; nullmailer(a)lists.untroubled.org Subject: Re: [stunnel-users] Stunnel 4 failing to connect to gmail On Mon, Dec 15, 2008 at 4:49 PM, Scott Gifford <sgifford(a)suspectclass.com> wrote: > "Asif Iqbal" <vadud3(a)gmail.com> writes: > > [...] > >> I said it too soon. It passed that bind error but it still failing in ssl. >> I am seeing `SSL alert (write): fatal: handshake failure' > > Hello again Asif, glad you decided to try out stunnel! Yep, as you suggested :-) > > Try using port 465 instead of 587. That worked! I were able to send an email and I did receive it. It says the email came from `vadud3(a)gmail.com' instead of the sender, which is me(a)myhomecomputer.domain I am using this in /etc/nullmailer/remotes file localhost smtp --port=25 --user=vadud3 --pass=s3cr3t > > It looks like Google's STARTTLS command requires an EHLO to be sent > first, which is a someqhat unusual requirement. I don't think stunnel > does that. Port 465 will start talking SSL directly, without > requiring SMTP commands first. > > Good luck! > > ----Scott. > -- Asif Iqbal PGP Key: 0xE62693C5 KeyServer: pgp.mit.edu _______________________________________________ stunnel-users mailing list stunnel-users(a)mirt.net http://stunnel.mirt.net/mailman/listinfo/stunnel-users

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Re: [stunnel-users] Cannot connect to SBC/yahoo to send (or telnet)
by Leandro Avila 12 Dec '08

12 Dec '08

Not sure if ranting will get you the kind of answer that you look for but it was certainly entertaining for me. Anyway... I agree, some times things can be a little frustraiting but I guess that depends on how much time on how much work you want to put into it. Sorry to hear you feel stupid. Everyone has to start from 0 at shome point and it takes time to get a good handle to how things work. The question is... do you really want to know how things work or just want them to work without having to do much? A google search of "SSL Explained" http://wildbill.nulldevice.net/presentations/sslpreso/ I liked slide 11/35 nice little diagram of SSL handshake wich helps to visualize in very general terms how an SSL connection works. The rest of the slides are good too check them out! In your particular case that forced you to change from plain-text to SSL connections to your mail server. You had a couple of options. - First and most obvious is to use SSL support build into your mail client (Thunderbird, Outlook,etc) most if not all modern mail clients support SSL natively. No need for stunnel there. - If your mail client does not support SSL then stunnel is the way to go. But your issue is on how stunnel is being used. As client. When you are a client... you always want to verify your server. You want to make sure you are connected to the right server. You want to use verify=2 in stunnel.conf How do we verify that the server I just connected is in fact the right server? That is the Certificate Authority's job. We ultimately have to trust the CA they issued the certificate for the server owner. They signed the certificate with their key. and we use the CA's certificate to verify that signature. Here is the catch... operating systems, and some programs are shipped with a prebuild collection of CA certificates. Unfortunatelly stunnel does not. However, most CAs let you download their certificates for your own use. In your particular case, looks like the server you are connecting to uses a certificate issued by Equifax Secure Certificate Authority Here they have the download page for the CA Certificates. http://www.geotrust.com/resources/root-certificates/ You pointed out that they refuse connections if the client presents a certificate. Yes, that is somehow a common practice. Mutual authentication (both server and client send certificates to each other and verify them) is impractical in some cases. Thanks ----------------- Leandro Avila

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