Gmail smtp openssl wtf error

[katokato]

so im trying to send email by talking to smtp server
the problem is that when i type in data it says its unrecognized!?!?!?!??! wAT THe fu** is that? I mean its the most basic fuc*ing command???!?!?!
I searched for hours and nothing came up like this.
Im using open ssl.
Here is what i did:

C:\OpenSSL-Win32\bin>openssl
WARNING: can't open config file: /usr/local/ssl/openssl.cnf
OpenSSL> s_client -crlf -connect smtp.gmail.com:465
Loading 'screen' into random state - done
CONNECTED(00000300)
depth=1 C = US, O = Google Inc, CN = Google Internet Authority
verify error:num=20:unable to get local issuer certificate
verify return:0
---
Certificate chain
0 s:/C=US/ST=California/L=Mountain View/O=Google Inc/CN=smtp.gmail.com
i:/C=US/O=Google Inc/CN=Google Internet Authority
1 s:/C=US/O=Google Inc/CN=Google Internet Authority
i:/C=US/O=Equifax/OU=Equifax Secure Certificate Authority
---
Server certificate
-----BEGIN CERTIFICATE-----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=
-----END CERTIFICATE-----
subject=/C=US/ST=California/L=Mountain View/O=Google Inc/CN=smtp.gmail.com
issuer=/C=US/O=Google Inc/CN=Google Internet Authority
---
No client certificate CA names sent
---
SSL handshake has read 2066 bytes and written 443 bytes
---
New, TLSv1/SSLv3, Cipher is ECDHE-RSA-RC4-SHA
Server public key is 1024 bit
Secure Renegotiation IS supported
Compression: NONE
Expansion: NONE
SSL-Session:
Protocol : TLSv1
Cipher : ECDHE-RSA-RC4-SHA
Session-ID: 07C3D1507F98D7CFBA7C60CB954E15B91F268C09EA9E7CA9A1B581747AF69266

Session-ID-ctx:
Master-Key: 11EF5035C5310BAA043210545295ED94B684B6061495C166241353C71D4E09F9
9A93499F848608322F77F7A0AE17DE1E
Key-Arg : None
PSK identity: None
PSK identity hint: None
SRP username: None
TLS session ticket lifetime hint: 100800 (seconds)
TLS session ticket:
0000 - 75 be ab 14 ff bf e3 74-61 4f 98 e6 ec 58 ae ab u......taO...X..
0010 - 16 1a d3 bf 9c 33 b6 78-7d 27 d7 f4 ab dc d4 e7 .....3.x}'......
0020 - 1e 6b e2 3b 35 01 49 1e-60 89 0c be 6b 79 97 bb .k.;5.I.`...ky..
0030 - 72 85 6f 1f 84 af 4a 1a-dd df 9c ce b6 9a a7 b7 r.o...J.........
0040 - db 2e 47 84 97 4e c8 62-1c d8 12 74 0c 2f 95 fd ..G..N.b...t./..
0050 - 7d 97 df 71 fb ec c9 a2-73 ea ae ba 50 e7 ff db }..q....s...P...
0060 - c5 7a 28 7f 5b 74 20 79-80 e4 15 35 87 7d c3 88 .z(.[t y...5.}..
0070 - d8 d6 f6 9b 8d 58 44 32-6d 65 80 34 9a 98 1a cf .....XD2me.4....
0080 - dd 0c db 43 13 7e 72 e8-1e 04 1d f4 d3 9c 2a af ...C.~r.......*.
0090 - 72 0b 82 d4 r...

Start Time: 1333938046
Timeout : 300 (sec)
Verify return code: 20 (unable to get local issuer certificate)
---
220 mx.google.com ESMTP b2sm14870994obo.22

502 5.5.1 Unrecognized command. b2sm14870994obo.22
EHLO TESTING
250-mx.google.com at your service, [99.109.89.125]
250-SIZE 35882577
250-8BITMIME
250-AUTH LOGIN PLAIN XOAUTH
250 ENHANCEDSTATUSCODES
AUTH LOGIN a2Vsdmluc2lsdmE3NDdAZ21haWwuY29t
334 UGFzc3dvcmQ6
MjIwNzNra2trDQo=
235 2.7.0 Accepted
mail from: <obama@usgov.gov>
250 2.1.0 OK b2sm14870994obo.22
data
502 5.5.1 Unrecognized command. b2sm14870994obo.22
rcpt to: <tster1@live.com>
250 2.1.5 OK b2sm14870994obo.22
data
502 5.5.1 Unrecognized command. b2sm14870994obo.22
DATA
502 5.5.1 Unrecognized command. b2sm14870994obo.22

so how the fu** do i fix this bs????
why is data not working to put in my message???

 

[Cyberat_88]

My question is why do you come cursing with an attitude about an error in LINUX/UNIX, to the XP troubleshooting forum ? Go rage at the Kernel builders for your particular Linux "flavor" of the month. Linux sucks ! It's free, but the community builders have a square IN THE BOX mentality of building like Windows.... Drivers are so 1980s, if you need drivers, kernel should build them, not import, not use dbs, etc... crap makes Linux incompatible with most hardware, depending on time and which distribution you pick. Also they need to build a reliable MBR with dual boot, they all end up corrupting and destroying the system. That's my linux rant.

 

[katokato]

im not even using linux.
im using windows xp with openssl trying to use smtp google server
i input all things correctly but most basic command on the book doesn't work
so what am i doing wrong?
im just frustrated that im doing everything correctly and just some random bullshit fucks up my entire way of email.
btw linux is a great kernel with lots of different oses. I like linux but atm im using windows since i game on it. and dual booting with linux is easy and simple???

 

[Cyberat_88]

Never easy never simple, corrupted half dozen pc's mbrs from puppy, to redhad, suse and more. Always incompatible with some hardware in the PC making it useless.
"C:\OpenSSL-Win32\bin>openssl
WARNING: can't open config file: /usr/local/ssl/openssl.cnf"
What's wrong with this picture ? You are running the Linux version of OpenSSL in Windows, it's looking for typical Linux directories and files in your Windows PC....

 

[Cyberat_88]

On top of that using certificates to send mail as "obama@usgov.gov" as a spoof.

 

[katokato]

lol yes because the folder is titled openssl-WIN32!!!!!
its only the config file that cant open, ti doesnt affect the way the program runs, its only for things if i save a server or a password etc.

 

[Cyberat_88]

You are then aware that some Linux distros have windows mode and this may have been designed for the Linux Wine mode. I say get a better app. this was clearly written by a rookie programmer.

 

[Guest]

I just solved this.. was dealing with the same problem for a while! You need to remove the '-crlf' from the openssl invokation. Also, you probably want to remove the base64 encoding of your username and password.