An Introduction to OpenSSL Programming (Part I)

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1

Introduction

The quickest and easiest way to secure a TCP-based network application is with SSL. If you’re

working in C, your best choice is probably to use OpenSSL, (the web site is at

http://www.openssl.org/). OpenSSL is a free (BSD-style license) implementation of

SSL/TLS based on Eric Young’s SSLeay package. Unfortunately, the documentation and sample

code distributed with OpenSSL leaves something to be desired. Where they exist, the manual

pages are pretty good, but they often miss the big picture, as manual pages are intended as a reference, not a tutorial.

We provide an introduction to OpenSSL programming. The OpenSSL API is vast and com-

plicated so we don’t attempt to provide anything like complete coverage. Rather, the idea is to

teach you enough to work effectively from the manual pages. In this article, the first of two, we

build a simple Web client and server pair that demonstrates the basic features of OpenSSL. In

the second article we introduce a number of advanced features, such as session resumption and

client authentication.

We assume that you’re already familiar with SSL and HTTP at least at a conceptual level. If

you’re not, a good place to start is with the RFCs (see the end of this article for references).

2

Source Code

For space reasons, this article only includes excerpts from the source code. The complete source

code is available in machine-readable format from the author’s web site at

http://www.rtfm.com/openssl-examples/

3

Our Programs

Our client is a simple HTTPS (see RFC 2818) client. It initiates an SSL connection to the server

and then transmits an HTTP request over that connection. It then waits for the response from the

server and prints it to the screen. This is a vastly simplified version of the functionality found in

programs like fetch and cURL.

The server program is a simple HTTPS server. It waits for TCP connections from clients.

When it accepts one it negotiates an SSL connection. Once the connection is negotiated, it reads

the client’s HTTP request. It then transmits the HTTP response to the client. Once the response

is transmitted it closes the connection.

3.1

Context Initialization

Our first task is to set up a context object (an SSL_CTX). This context object is then used to create a new connection object for each new SSL connection. It is these connection objects which

are used to do SSL handshakes, reads, and writes.

This approach has two advantages. First, the context object allows many structures to be ini-

tialized only once, improving performance. In most applications, every SSL connection will use

This article is Copyright © 2001 Eric Rescorla. It may be redistributed for any purpose and without fee provided

that this notice is retained. An earlier version of this article first appeared in the September 2001 issue of Linux Journal.

the same keying material, certificate authority (CA) list, etc. Rather than reloading this material

for every connection, we simply load it into the context object at program startup. When we

wish to create a new connection, we can simply point that connection to the context object. The

second advantage of having a single context object is that it allows multiple SSL connections to

share data, such as the SSL session cache used for session resumption.

Context initialization consists of four primary tasks, all performed by the initialize_ctx() function, shown in Figure 1.

SSL_CTX *initialize_ctx(keyfile,password)
 char *keyfile;
 char *password;
 {
 SSL_METHOD *meth;
 SSL_CTX *ctx;

 if(!bio_err){
 /* Global system initialization*/
 SSL_library_init();
 SSL_load_error_strings();

/* An error write context */
bio_err=BIO_new_fp(stderr,BIO_NOCLOSE);
}

 /* Set up a SIGPIPE handler */
 signal(SIGPIPE,sigpipe_handle);

 /* Create our context*/
 meth=SSLv23_method();
 ctx=SSL_CTX_new(meth);

 /* Load our keys and certificates*/
 if(!(SSL_CTX_use_certificate_chain_file(ctx, keyfile)))
 berr_exit("Can’t read certificate file");

 pass=password;
 SSL_CTX_set_default_passwd_cb(ctx,password_cb);

if(!(SSL_CTX_use_PrivateKey_file(ctx, keyfile,SSL_FILETYPE_PEM)))
 berr_exit("Can’t read key file");

 /* Load the CAs we trust*/
 if(!(SSL_CTX_load_verify_locations(ctx,CA_LIST,0)))
   berr_exit("Ca’t read CA list");
#if (OPENSSL_VERSION_NUMBER < 0x0090600fL)
SSL_CTX_set_verify_depth(ctx,1);
#endif

return ctx;
}

Figure 1 initialize_ctx()

Initialize the library and create the context

Before OpenSSL can be used for anything, the library as a whole must be initialized. This is

accomplished with SSL_library_init(), which primarily loads up the algorithms that

OpenSSL will be using. If we want good reporting of errors, we also need to load the error

strings using SSL_load_error_strings(). Otherwise, we won’t be able to map

OpenSSL errors to strings.

We also create an object to be used as an error printing context. OpenSSL uses an abstraction called a BIO object for input and output. This allows the programmer to use the same functions for different kinds of I/O channels (sockets, terminal, memory buffers, etc.) merely by using different kinds of BIO objects. In this case we create a BIO object attached to stderr to be used for printing errors.

Load our own keys

If you’re writing server--or a client which is able to perform client authentication--you’ll need to

load your own public/private key pair and the associated certificate. The certificate is stored in

the clear and is loaded together with the CA certificates forming the certificate chain using

SSL_CTX_use_certificate_chain_file(). We use SSL_CTX_use_PrivateKey_file() to load the private key. For security reasons, the private key is usually encrypted

under a password. If the key is encrypted, the password callback (set using SSL_CTX_set_default_passwd_cb()) will be called to obtain the password.

Load root CA list

If you’re going to be authenticating the host you’re connected to OpenSSL needs to know what

certificate authorities (CAs) you trust. The SSL_CTX_load_verify_locations() call is used to load the CAs.

Load Randomness

In order to have good security, SSL needs a good source of strong random numbers. In general,

it’s the responsibility of the application to supply some seed material for the random number

generator. However, OpenSSL automatically uses /dev/urandom to seed the RNG, if it is

available. Since /dev/urandom is standard on Linux, we don’t have to do anything for

this--which is convenient since gathering random numbers is tricky and easy to screw up. Note

that if you’re on a system other than Linux you may get an error at some point because the random number generator is unseeded. OpenSSL’s rand(3) manual page provides more information.

4

The Client

Once the client has initialized the SSL context, it’s ready to connect to the server. OpenSSL

requires us to create a TCP connection between client and server on our own and then use the

TCP socket to create an SSL socket. For convenience we’ve isolated the creation of the TCP

connection to the tcp_connect() function (which is not shown here but is available in the

downloadable source).

Once the TCP connection has been created, we create an SSL object to handle the connec-

tion. This object needs to be attached to the socket. Note that that we don’t directly attach the

SSL object to the socket. Rather, we create a BIO object using the socket and then attach the

SSL object to the BIO.

This abstraction layer allows you to use OpenSSL over channels other than sockets, pro-

vided you have an appropriate BIO. For instance, one of the OpenSSL test programs connects

an SSL client and server purely through memory buffers. A more practical use would be to sup-

port some protocol that can’t be accessed via sockets. For instance, you could run SSL over a

serial line.

Handshake

The first step in an SSL connection is to perform the SSL handshake. The handshake authenti-

cates the server (and optionally the client) and establishes the keying material that will be used

to protect the rest of the traffic. The SSL_connect() call is used to perform the SSL hand-

shake. Because we’re using blocking sockets, SSL_connect() will not return until the hand-

shake is completed or an error has been detected. SSL_connect() returns 1 for success and 0

or negative for an error. This call is shown in Figure 2.

/* Connect the TCP socket*/
 sock=tcp_connect(host,port);

 /* Connect the SSL socket */
 ssl=SSL_new(ctx);
 sbio=BIO_new_socket(sock,BIO_NOCLOSE);
 SSL_set_bio(ssl,sbio,sbio);
 if(SSL_connect(ssl)<=0)
  berr_exit("SSL connect error");
 if(require_server_auth)
 check_cert(ssl,host);

Figure 2 connecting to the server

Server Authentication

When we initiate an SSL connection to a server, we need to check the server’s certificate chain.

OpenSSL does some of the checks for us but unfortunately some of the checks are application

specific and so we have to do those ourselves. The primary test that our sample application does

is to check the server identity. This check is performed by the check_cert() function, shown

in Figure 3.

void check_cert(ssl,host)
 SSL *ssl;
 char *host;
 {
 X509 *peer;
 char peer_CN[256];


if(SSL_get_verify_result(ssl)!=X509_V_OK)
berr_exit("Certificate doesn’t verify");


/*Check the cert chain. The chain length  is automatically checked by OpenSSL when  we set the verify depth in the ctx */

 /*Check the common name*/
 peer=SSL_get_peer_certificate(ssl);
 X509_NAME_get_text_by_NID (X509_get_subject_name(peer),
                NID_commonName, peer_CN, 256);
 if(strcasecmp(peer_CN,host))
 err_exit("Common name doesn’t match host name");
}

Figure 3 check_cert() function

Server Identity

Once you’ve established that the server’s certificate chain is valid, you need to verify that the

certificate you’re looking at matches the identity that we expect the server to have. In most

cases, this means that the server’s DNS name appears in the certificate, either in the Common

Name field of the Subject Name or in a certificate extension. Although each protocol has slightly

different rules for verifying the server’s identity, RFC 2818 contains the rules for HTTP over

SSL/TLS. Following RFC 2818 is generally a good idea unless you have some explicit reason to

do otherwise. to

Since most certificates still contain the domain name in Common Name rather than an

extension, we show only the Common Name check. We simply extract the server’s certificate

using SSL_get_peer_certificate() and then compare the common name to the host

name we’re connecting to. If they don’t match, something is wrong and we exit.

Chain Length

Before version 0.9.5, OpenSSL was subject to a certificate extension attack. To see what this is,

consider the case where you a server authenticates with a certificate signed by Bob, as shown in

Figure 4. Bob isn’t one of your CAs but his certificate is signed by a CA you trust.

Root

CA

Bob

Server

Figure 4 An extended certificate chain

If you accept this certificate you’re likely going to be in a lot of trouble. The fact that the CA

signed Bob’s certificate means that the CA believes that it has verified Bob’s identity, not that

Bob can be trusted. If you know that you want to do business with Bob, that’s fine, but it’s not

very useful if you want to do business with Alice and Bob (who you’ve never heard of) is vouching for Alice.

Originally, the only way to protect yourself against this sort of attack was to restrict the

length of certificate chains so that you knew that the certificate you’re looking at was signed by

the CA. X.509 version 3 contains a way for a CA to label certain certificates as other CAs. This

permits a CA to have a single root that then certifies a bunch of subsidiary CAs.

Modern versions of OpenSSL (0.9.5 and later) check these extensions so you’re automati-

cally protected against extension attacks whether or not you check chain length. Versions prior

to 0.9.5 do not check the extensions at all, so you have to enforce the chain length if using an

older version. 0.9.5 has some problems with checking so if you’re using 0.9.5, you should probably upgrade. The #ifdef-ed code in initialize_ctx() provides chain length checking

with older versions. We use the SSL_CTX_set_verify_depth() to force OpenSSL to

check the chain length. In summary, it’s highly advisable to upgrade to 0.9.6, particularly since

longer (but properly constructed) chains are becoming more popular.

When To Check Certicates

The code shown here allows the entire handshake to complete, whether or not the peer has a

valid certificate. It’s important to note that this is not the only way to check the server’s

certificate. Only after the handshake completes do we check the certificate and possibly terminate the connection. This approach has the advantage that it’s easy to implement but the disadvantage that if we don’t like the server’s certificate the server just sees a generic error rather than one indicating that the certificate was bad.

An alternative is to use the SSL_CTX_set_verify() API call to have OpenSSL require

valid certificates during the handshake—if the server presents an invalid certificate the hand-

shake will fail and the server will receive an error indicating that it had a bad certificate. You can

also use SSL_CTX_set_verify() to set a callback to be called during certificate checking,

allowing you to apply extra checks or permit certificates which OpenSSL might otherwise not

accept.

Request

We use the code shown in Figure 5 to write the HTTP request. For demonstration purposes, we

use a more-or-less hardwired HTTP request, found in the REQUEST_TEMPLATE variable.

Because the machine we’re connecting to may change we do need to fill in the Host header.

This is done using the sprintf() in line 30. We then use SSL_write() to send the data to

the server. SSL_write()as write(), except that we pass in the SSL object instead of the

file descriptor.

Experienced TCP programmers will notice that instead of looping around the write we

throw an error if the return value doesn’t equal the value we’re trying to write. In blocking

mode, SSL_write() semantics are ’all-or-nothing’: the call won’t return until all the data is

written or an error occurs, whereas write() may only write part of the data.

Note: The SSL_MODE _ENABLE_PARTIAL_WRITE flag (not used here) enables partial

writes, in which case you’d need to loop.

Response

In old-style HTTP/1.0, the server transmits its response and then closes the connection. In later

versions, persistent connections that allow multiple sequential transactions on the same connec-

tion were introduced. For convenience and simplicity we will not use persistent connections. We

omit the header that allows them, causing the server to use a connection close to signal the end

of the response. Operationally, this means that we can keep reading until we get an end of file,

which simplifies matters considerably.

OpenSSL uses the SSL_read() API call to read data, as shown in Figure 6. As with

read() we simply choose an appropriate sized buffer and pass it to SSL_read(). Note that

the buffer size isn’t really that important here. The semantics of SSL_read(), like the seman-

tics of read(), are that it returns the data available, even if it’s less than the requested amount.

On the other hand, if no data is available, then the call to read blocks.

The choice of BUFSIZZ, then, is basically a performance tradeoff. The tradeoff is quite different here than when we’re simply reading from normal sockets. In that case, each call to read() requires a context switch into the kernel. Because context switches are expensive, programmers try to use large buffers to reduce them. However, when we’re using SSL the number of calls to read()—and hence context switches—is largely determined by the number of records the data was written in rather than the number of calls to SSL_read().

request_len=strlen(REQUEST_TEMPLATE)+strlen(host)+6;
if(!(request=(char *)malloc(request_len)))
  err_exit("Couldn’t allocate request");
sprintf(request,REQUEST_TEMPLATE,host,port);

 /* Find the exact request_len */
request_len=strlen(request);

 r=SSL_write(ssl,request,request_len);
 switch(SSL_get_error(ssl,r)){
 case SSL_ERROR_NONE:
   if(request_len!=r)
     err_exit("Incomplete write!");
   break;
 default:
   berr_exit("SSL write problem");
}

Figure 5 writing the HTTP request

For instance, if the client wrote a 1000-byte record and we call SSL_read() in chunks of 1

byte, then the first call to SSL_read() will result in the record being read

in and the rest of the calls will just read it out of the SSL buffer. Thus, the choice of buffer size

is less significant when we’re using SSL than with normal sockets.

Note that if the data were written in a series of small records, you might want to read

all of them at once with a single call to read(). OpenSSL provides a flag

SSL_CTRL_SET_READ_AHEAD that turns on this behavior.

while(1){
  r=SSL_read(ssl,buf,BUFSIZZ);
    switch(SSL_get_error(ssl,r)){
      case SSL_ERROR_NONE:
       len=r;
       break;
      case SSL_ERROR_ZERO_RETURN:
        goto shutdown;
      case SSL_ERROR_SYSCALL:
         fprintf(stderr,"SSL Error: Premature close0);
        goto done;
      default:
        berr_exit("SSL read problem");
 
    }
 
fwrite(buf,1,len,stdout);
}

Figure 6 reading the response

Note the use of the switch on the return value of SSL_get_error() in line 12. The con-

vention with normal sockets is that any negative number (typically −1) indicates failure and that

one then checks errno to determine what actually happened. Obviously errno won’t work

here since that only shows system errors and we’d like to be able to act on SSL errors. Also,

errno requires careful programming in order to be thread safe.

Instead of errno, OpenSSL provides the SSL_get_error() call. This call lets us

examine the return value and figure out whether an error occurred and what it was. If the return

value was positive, we’ve read some data and we simply write it to the screen. A real client

would of course parse the HTTP response and either display the data (e.g. a web page) or save it

to disk. However, none of this is interesting as far as OpenSSL is concerned so we don’t show

any of it.

If the return value was zero, this does not mean that there was no data available. In that case,

we would have blocked as discussed above. Rather, it means that the socket is closed and there

will never be any data available to read. Thus, we exit the loop.

Error Handling

If the return value was something negative then some kind of error occurred. There are two

kinds of errors we’re concerned with: ordinary errors and "premature closes". We use the

SSL_get_error() call to determine which kind of error we have. Error handling in our

client is pretty primitive so with most errors we simply call berr_exit() to print an error

message and exit. Premature closes have to be handled specially.

Closure

TCP uses a FIN segment to indicate that the sender has sent all of its data. SSL version 2 simply

allowed either side to send a TCP FIN to terminate the SSL connection. This allowed for a

"truncation attack": the attacker could make it appear that a message was shorter than it was

simply by forging a TCP FIN. Unless the victim had some other way of knowing what message

length to expect it would simply believe that it had received a shorter message.

In order to prevent this security problem, SSLv3 introduced a close_notify alert. The

close_notify is an SSL message (and therefore secured) but is not part of the data stream itself

and so is not seen by the application. No data may be transmitted after the close_notify is sent.

Thus, when SSL_read() returns 0 to indicate that the socket has been closed, this really

means that the close_notify has been received. If the client receives a FIN before receiving a

close_notify, SSL_read() will return with an error. This is called a "premature close".

A naive client might decide to report an error and exit whenever it received a premature

close. This is the behavior that is implied by the SSLv3 specification. Unfortunately, sending

premature closes is a rather common error, particularly common with clients. Thus, unless you

want to be reporting errors all the time you often have to ignore premature closes. Our code

splits the difference. It reports the premature close on stderr but doesn’t exit with an error.

Shutdown

If we read the response without any errors then we need to send our own close_notify to the

server. This is done using the SSL_shutdown() API call. We’ll cover SSL_shutdown()

more completely when we talk about the server but the general idea is simple: it returns 1 for a

complete shutdown, 0 for an incomplete shutdown, and -1 for an error. Since we’ve already

received the server’s close_notify, about the only thing that can go wrong is that we have trouble

sending our close_notify. Otherwise SSL_shutdown() will succeed (returning 1).

Cleanup

Finally, we need to destroy the various objects we’ve allocated. Since this program is about to

exit, freeing the objects automatically, this isn’t strictly necessary, but would be in a real program.

5

Server

Our web server is mainly a mirror of the client, but with a few twists. First, we fork() in order

to let the server handle multiple clients. Second, we use OpenSSL’s BIO APIs to read the

client’s request one line at a time, as well as to do buffered writes to the client. Finally, the

server closure sequence is more complicated.

Accept and Fork

On Linux, the simplest way to write a server that can handle multiple clients is to create a new

server process for each client that connects. We do that by calling fork() after accept()

returns. Each new process executes independently and just exits when it’s finished serving the

client. Although this approach can be quite slow on busy web servers it’s perfectly acceptable

here. The main server accept loop is shown in Figure 7.

 

while(1){
 
if((s=accept(sock,0,0))<0)
    err_exit("Problem accepting");
 
if((pid=fork())){
 close(s);
  }
  else {
  sbio=BIO_new_socket(s,BIO_NOCLOSE);
  ssl=SSL_new(ctx);
  SSL_set_bio(ssl,sbio,sbio);
 
 
if((r=SSL_accept(ssl)<=0))
    berr_exit("SSL accept error");
 
http_serve(ssl,s);
 
exit(0);
 
}
}

Figure 7 server accept loop

Server Accept

After forking and creating the SSL object, the server calls SSL_accept() which causes

OpenSSL to perform the server side of the SSL handshake. As with SSL_connect(),

because we’re using blocking sockets, SSL_accept() will block until the entire handshake

has completed. Thus, the only situation in which SSL_accept() will return is when the hand-

shake has completed or an error has been detected. SSL_accept() returns 1 for success and 0

or negative for error.

Buffered I/O

OpenSSL’s BIO objects are to some extent stackable. Thus, we can wrap an SSL object in a

BIO (the ssl_bio object) and then wrap that BIO in a buffered BIO object, as shown in Fig-

ure 8. This allows us to perform buffered reads and writes on the SSL connection by using the

BIO_* functions on the new io object. At this point you might ask: why is this good? Primarily,

it’s a matter of programming convenience: It lets the programmer work in natural units (lines

and characters) rather than SSL records.

13 io=BIO_new(BIO_f_buffer());
14 ssl_bio=BIO_new(BIO_f_ssl());
15 BIO_set_ssl(ssl_bio,ssl,BIO_CLOSE);
16 BIO_push(io,ssl_bio);

Figure 8 creating a buffered BIO

Request

An HTTP request consists of a request line followed by a bunch of header lines and an optional

body. The end of the header lines is indicated by a blank line (i.e., a pair of CRLFs, though

sometimes broken clients will send a pair of LFs instead). The most convenient way to read the

request line and headers is to read one line at a time until you see a blank line. We can do this

using the OpenSSL BIO_gets() call, as shown in Figure 9.

The BIO_gets() call behaves analogously to the stdio fgets() call. It takes an arbi-

trary size buffer and a length and reads a line from the SSL connection into that buffer. The

result is always null terminated (but includes the terminating LF). Thus, we simply read one line

at a time until we get a line which consists of simply a LF or a CRLF.

Because we use a fixed length buffer, it is possible though unlikely that we will get an over-

long line. In that event the long line will be split over two lines. In the (extremely unlikely) event

that the split happens right before the CRLF, the next line we read will consist only of the CRLF

from the previous line. In this case we’ll be fooled into thinking that the headers have finished

prematurely. A real Web server would check for this case but it’s not worth doing here. Note that

no matter what the incoming line length there’s no chance of a buffer overrun. All that can hap-

pen is that we’ll misparse the headers.

Note that we don’t really DO anything with the HTTP request. We just read it and discard it.

A real implementation would read the request line and the headers, figure out of there was a

body and read that too. However, none of these things show anything interesting about SSL so

they don’t add anything to this demonstration.

18
while(1){
19
r=BIO_gets(io,buf,BUFSIZZ-1);
20
21
switch(SSL_get_error(ssl,r)){
22
case SSL_ERROR_NONE:
23
len=r;
24 break;
25 default:
26
berr_exit("SSL read problem");
27
}
28
29
/* Look for the blank line that signals
30
the end of the HTTP headers */

31
if(!strcmp(buf,"0) ||!strcmp(buf,"0))
33
34
break;
}

Figure 9 reading the request

Response

The next step is to write the HTTP response and close the connection. Figure 10 shows this

code. Note that we’re using BIO_puts() instead of SSL_write(). This allows us to write

the response one line at a time but have the entire response written as a single SSL record. This

is important because the cost of preparing an SSL record for transmission (computing the

integrity check and encrypting it) is quite significant. Thus, it’s a good idea to make the records

as large as possible.

It’s worth noting a couple of subtleties about using this kind of buffered write:

1. You need to flush the buffer before you close. The SSL object has no knowledge that you’ve

layered a BIO on top of it, so if you destroy the SSL connection you’ll just leave the last

chunk of data sitting in the buffer. The BIO_flush() call in line 46 takes care of this.

2. By default, OpenSSL uses a 1024-byte buffer size for buffered BIOs. Because SSL records

can be up to 16K bytes long, using a 1024-byte buffer cause excessive fragmentation (and

hence lower performance.) You can use the BIO_ctrl() API to increase the buffer size.

if((r=BIO_puts
(io,"HTTP/1.0 200 OK\r\n"))<0)
err_exit("Write error");
if((r=BIO_puts
(io,"Server: EKRServer\r\n\r\n"))<0)
err_exit("Write error");
if((r=BIO_puts
43 (io,"Server test page\r\n"))<0)
44 err_exit("Write error");
45
46
47
if((r=BIO_flush(io))<0)
err_exit("Error flushing BIO");

Figure 10 writing the response

Shutdown

Once we’ve finished transmitting the response we need to send our close_notify. As before, this

is done using SSL_shutdown(). Unfortunately, things get a bit trickier when the server

closes first. Our first call to SSL_shutdown() sends the close_notify but doesn’t look for it on

the other side. Thus, it returns immediately but with a value of 0, indicating that the closure

sequence isn’t finished. It’s then the application’s responsibility to call SSL_shutdown()

again.

It’s possible to have two attitudes here:

1. We’ve seen all of the HTTP request that we care about. we’re not interested in anything else.

Hence, we don’t care whether the client sends a close_notify or not.

2. We strictly obey the protocol and expect others to as well. Thus, we require a close_notify.

If we have the first attitude then life is simple: We call SSL_shutdown() to send our

close_notify and then exit right away, regardless of whether the client has sent one or not. If we

take the second attitude (which our sample server does), then life is more complicated, because

clients often don’t behave correctly.

The first problem we face is that client’s often don’t send close_notifys all. In fact, some

clients close the connection as soon as they’ve read the entire HTTP response (some versions of

IE do this). When we send our close_notify, the other side may send a TCP RST segment, in

which case the program will catch a SIGPIPE. We install a dummy SIGPIPE handler in ini-

tialize_ctx() to protect against this problem.

The second problem we face is that the client may not send a close_notify immediately in

response to our close_notify. Some versions of Netscape require you to send a TCP FIN first.

Thus, we call shutdown(s,1) before we call SSL_shutdown() the second time. When

called with a "how" argument of 1, shutdown() sends a FIN but leaves the socket open for

reading. The code to do the server shutdown is shown in Figure 11 (see next page).

6

What’s Missing

In this article, we’ve only scratched the surface of the issues involved with using OpenSSL.

Here’s a (non-exhaustive) list of additional issues.

Better Certificate Checking

A more sophisticated approach to checking server certificates against the server hostname is to

use the X.509 subjectAltName extension. In order to make this check, you would need to extract

this extension from the certificate and then check it against the hostname. Additionally, it would

be nice to be able to check host names against wildcarded names in certificates. We don’t show

how to do this either.

51 r=SSL_shutdown(ssl);
52 if(!r){
53
/* If we called SSL_shutdown() first then
54 we always get return value of ’0’. In
55 this case, try again, but first send a
56 TCP FIN to trigger the other side’s
57
close_notify*/
58
shutdown(s,1);
59
60
r=SSL_shutdown(ssl);
}
61
62
switch(r){
63
case 1:
64
break; /* Success */
65 case 0:
66 case -1:
67 default:
68
69
berr_exit("Shutdown failed");
}

Figure 11 calling SSL_shutdown()

Better Error Handling

Note that these applications handle errors simply by exiting with an error. A real application

would, of course, be able to recognize errors and signal them to the user or some audit log rather

than just exiting.

6.1

Coming Soon

In the second part, we’ll be discussing a number of advanced OpenSSL features, including...

Session Resumption

SSL handshakes are expensive but SSL provides a feature called session resumption that allows

you to bypass the full handshake for a peer you’ve communicated with before.

Multiplexed and Non-blocking I/O

We used blocking sockets for all of our reads and writes. This means that while the application

is waiting for data from the peer it’s completely stalled. This wouldn’t be acceptable in a real

GUI application like a browser. Instead, you need to use the select() call to multiplex

between SSL and other sources of I/O.

Client Authentication

Server authentication occurs as a part of almost every SSL connection. However, SSL also offers

certificate-based client authentication, at the server’s request.

6.2

External Resources

Parts of this article were adapted from my book "SSL and TLS: Designing and Building Secure

Systems", Addison-Wesley 2000. "SSL and TLS" offers a comprehensive guide to the SSL pro-

tocol and its applications. See http://www.rtfm.com/sslbook for more information.

Machine readable source code for the programs presented here can be downloaded from the

author’s web site at: http://www.rtfm.com/openssl-examples/. The source code is

available under a BSD-style license.

You can get OpenSSL from http://www.openssl.org/. The docs are online here as well.

The relevant specifications are at:

SSLv2: http://www.netscape.com/eng/security/SSL_2.html

SSLv3: http://home.netscape.com/eng/ssl3/index.html

TLS (RFC 2246): http://www.ietf.org/rfc/rfc2246.txt

HTTPS (RFC 2818): http://www.ietf.org/rfc/rfc2818.txt

6.3

Acknowledgements

Thanks to Lisa Dusseault, Steve Henson, Lutz Jaenicke, and Ben Laurie for help with OpenSSL

and review of this article.

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