use strict;
use warnings;
use Socket;
use IO::Socket::SSL 1.984;
use IO::Socket::SSL::Utils;
use Getopt::Long qw(:config posix_default bundling);
my $can_ocsp = IO::Socket::SSL->can_ocsp;
my $ocsp_cache = $can_ocsp && IO::Socket::SSL::OCSP_Cache->new;
my %starttls = (
'' => [ 443,undef, 'http' ],
'smtp' => [ 25, \&smtp_starttls, 'smtp' ],
'http_proxy' => [ 443, \&http_connect,' http' ],
'http_upgrade' => [ 80, \&http_upgrade,'http' ],
'imap' => [ 143, \&imap_starttls,'imap' ],
'pop' => [ 110, \&pop_stls,'pop3' ],
'ftp' => [ 21, \&ftp_auth,'ftp' ],
'postgresql' => [ 5432, \&postgresql_init,'default' ],
);
my $verbose = 0;
my $timeout = 10;
my ($stls,$stls_arg);
my $capath;
my $all_ciphers;
my $show_chain;
my $dump_chain;
GetOptions(
'h|help' => sub { usage() },
'v|verbose:1' => \$verbose,
'd|debug:1' => \$IO::Socket::SSL::DEBUG,
'T|timeout=i' => \$timeout,
'CApath=s' => \$capath,
'show-chain' => \$show_chain,
'dump-chain' => \$dump_chain,
'all-ciphers' => \$all_ciphers,
'starttls=s' => sub {
($stls,$stls_arg) = $_[1] =~m{^(\w+)(?::(.*))?$};
usage("invalid starttls $stls") if ! $starttls{$stls};
},
);
@ARGV or usage("no hosts given");
my %default_ca =
! $capath ? () :
-d $capath ? ( SSL_ca_path => $capath, SSL_ca_file => '' ) :
-f $capath ? ( SSL_ca_file => $capath, SSL_ca_path => '' ) :
die "no such file or dir: $capath";
die "need Net::SSLeay>=1.58 for showing chain" if $show_chain
&& ! defined &IO::Socket::SSL::peer_certificates;
sub usage {
print STDERR "ERROR: @_\n" if @_;
print STDERR <<USAGE;
Analyze SSL connectivity for problems.
Usage: $0 [options] (host|host:port)+
Options:
-h|--help - this screen
-v|--verbose level - verbose output
-d|--debug level - IO::Socket::SSL/Net::SSLeay debugging
--CApath file|dir - use given dir|file instead of system default CA store
--all-ciphers - find out all supported ciphers
--show-chain - show certificate chain
--dump_chain - dump certificate chain, e.g. all certificates as PEM
--starttls proto[:arg] - start plain and upgrade to SSL with starttls protocol
(imap,smtp,http_upgrade,http_proxy,pop,ftp,postgresql)
-T|--timeout T - use timeout (default 10)
Examples:
$0 --show-chain --all-ciphers -v3 www.live.com:443
$0 --starttls http_proxy:proxy_host:proxy_port www.live.com:443
$0 --starttls imap mail.gmx.de
USAGE
exit(2);
}
my @tests;
for my $host (@ARGV) {
my ($ip,$port);
$host =~m{^(?:\[(.+)\]|([^:]+))(?::(\w+))?$} or die "invalid dst: $host";
$host = $1||$2;
my $st = $starttls{$stls ||''};
$port = $3 || $st->[0] || 443;
if ( $host =~m{:|^[\d\.]+$} ) {
$ip = $host;
$host = undef;
}
push @tests, [ $host||$ip,$port,$host,$st->[1],$st->[2] || 'default' ];
}
my $ioclass = IO::Socket::SSL->can_ipv6 || 'IO::Socket::INET';
for my $test (@tests) {
my ($host,$port,$name,$stls_sub,$scheme) = @$test;
VERBOSE(1,"checking host=$host port=$port".
($stls ? " starttls=$stls":""));
my $tcp_connect = sub {
my $tries = shift || 1;
my ($cl,$error);
my %ioargs = (
PeerAddr => $host,
PeerPort => $port,
Timeout => $timeout,
);
for(1..$tries) {
if ($stls_sub) {
last if $cl = eval { $stls_sub->(\%ioargs,$stls_arg) };
$error = $@ || 'starttls error';
$cl = undef;
} elsif ( $cl = $ioclass->new(%ioargs)) {
last;
} else {
$error = "tcp connect: $!";
}
}
$cl or die $error;
};
my @problems;
# basic connects without verification or any TLS extensions (SNI, OCSP)
# find out usable version and ciphers
my ($use_version,$version,$cipher);
BASE: for my $v (qw(
SSLv23:!TLSv1_2:!TLSv1_1:!TLSv1
SSLv23:!TLSv1_2:!TLSv1_1
SSLv23:!TLSv1_2
SSLv23
)) {
for my $ciphers ( '','HIGH:ALL' ) {
my $cl = &$tcp_connect;
if ( IO::Socket::SSL->start_SSL($cl,
SSL_version => $v,
SSL_verify_mode => 0,
SSL_hostname => '',
SSL_cipher_list => $ciphers,
)) {
$use_version = $v;
$version = $cl->get_sslversion();
$cipher = $cl->get_cipher();
VERBOSE(2,"version $v no verification, ciphers=$ciphers, no TLS extensions -> $version,$cipher");
} else {
VERBOSE(2,"version $v, no verification, ciphers=$ciphers, no TLS extensions -> FAIL! $SSL_ERROR");
if ( ! $ciphers && $v eq 'SSLv23' ) {
push @problems, "using default SSL_version $v, default ciphers -> $SSL_ERROR";
} elsif ( ! $ciphers ) {
push @problems, "using SSL_version $v, default ciphers -> $SSL_ERROR";
} else {
push @problems, "using SSL_version $v, ciphers $ciphers -> $SSL_ERROR";
}
last BASE if $version;
}
}
}
if ($version) {
VERBOSE(1,"successful connect with $version cipher=$cipher and no TLS extensions");
} else {
die "$host failed basic SSL connect: $SSL_ERROR\n";
}
my %conf = ( SSL_version => $version, SSL_cipher_list => $cipher );
# check if host accepts SNI
my $sni_status;
if ( $name && $version !~m{^TLS} ) {
VERBOSE(1,"disabling SNI because SSL version $version too low");
} elsif ($name) {
my $cl = &$tcp_connect;
if ( IO::Socket::SSL->start_SSL($cl, %conf,
SSL_verify_mode => 0,
SSL_hostname => $name,
)) {
VERBOSE(1,"SNI success");
$sni_status = 'ok';
$conf{SSL_hostname} = $name;
} else {
VERBOSE(1,"SNI FAIL!");
$sni_status = "FAIL: $SSL_ERROR";
push @problems, "using SNI (default) -> $SSL_ERROR";
}
}
# get chain info
my (@cert_chain,@cert_chain_nosni);
if ($show_chain || $dump_chain) {
for(
[ \%conf, \@cert_chain ],
! $conf{SSL_hostname} ? ()
: ([ { %conf, SSL_hostname => '' }, \@cert_chain_nosni ])
) {
my ($conf,$chain) = @$_;
my $cl = &$tcp_connect;
if ( IO::Socket::SSL->start_SSL($cl, %$conf,
SSL_verify_mode => 0
)) {
for my $cert ( $cl->peer_certificates ) {
my ($subject,$bits);
$subject = Net::SSLeay::X509_NAME_oneline(
Net::SSLeay::X509_get_subject_name($cert));
if ( !@$chain) {
my @san = $cl->peer_certificate('subjectAltNames');
for( my $i=0;$i<@san;$i++) {
$san[$i] = 'DNS' if $san[$i] == 2;
$san[$i] .= ":".splice(@san,$i+1,1);
}
$subject .= " SAN=".join(",",@san) if @san;
}
if (my $pkey = Net::SSLeay::X509_get_pubkey($cert)) {
$bits = eval { Net::SSLeay::EVP_PKEY_bits($pkey) };
Net::SSLeay::EVP_PKEY_free($pkey);
}
push @$chain,[
$bits||'???',
$subject,
join('|', grep { $_ } @{ CERT_asHash($cert)->{ocsp_uri} || []}),
PEM_cert2string($cert),
],
}
} else {
die "failed to connect with previously successful config: $SSL_ERROR";
}
}
# if same certificate ignore nosni
if (@cert_chain_nosni
&& $cert_chain_nosni[0][3] eq $cert_chain[0][3]) {
VERBOSE(2,"same certificate in without SNI");
@cert_chain_nosni = ();
}
}
# check verification against given/builtin CA w/o OCSP
my $verify_status;
my $cl = &$tcp_connect;
if ( IO::Socket::SSL->start_SSL($cl, %conf,
SSL_verify_mode => SSL_VERIFY_PEER,
SSL_ocsp_mode => SSL_OCSP_NO_STAPLE,
SSL_verifycn_scheme => 'none',
%default_ca
)) {
%conf = ( %conf, SSL_verify_mode => SSL_VERIFY_PEER, %default_ca );
if ( $cl->verify_hostname( $name,$scheme )) {
VERBOSE(1,"certificate verify success");
$verify_status = 'ok';
%conf = ( %conf,
SSL_verifycn_scheme => $scheme,
SSL_verifycn_name => $name,
);
} else {
my @san = $cl->peer_certificate('subjectAltNames');
for( my $i=0;$i<@san;$i++) {
$san[$i] = 'DNS' if $san[$i] == 2;
$san[$i] .= ":".splice(@san,$i+1,1);
}
VERBOSE(1,"certificate verify - name does not match:".
" subject=".$cl->peer_certificate('subject').
" SAN=".join(",",@san)
);
$verify_status = 'name-mismatch';
%conf = ( %conf, SSL_verifycn_scheme => 'none');
}
} else {
VERBOSE(1,"certificate verify FAIL!");
$verify_status = "FAIL: $SSL_ERROR";
push @problems, "using certificate verification (default) -> $SSL_ERROR";
}
# check with OCSP stapling
my $ocsp_staple;
if ( $can_ocsp && $verify_status eq 'ok' ) {
my $cl = &$tcp_connect;
$conf{SSL_ocsp_cache} = $ocsp_cache;
if ( IO::Socket::SSL->start_SSL($cl, %conf)) {
if ( ${*$cl}{_SSL_ocsp_verify} ) {
$ocsp_staple = 'got stapled response',
} else {
$ocsp_staple = 'no stapled response',
}
VERBOSE(1,"OCSP stapling: $ocsp_staple");
} else {
$ocsp_staple = "FAIL: $SSL_ERROR";
$conf{SSL_ocsp_mode} = SSL_OCSP_NO_STAPLE;
VERBOSE(1,"access with OCSP stapling FAIL!");
push @problems, "using OCSP stapling (default) -> $SSL_ERROR";
}
}
my $ocsp_status;
if ( $can_ocsp && $verify_status eq 'ok' ) {
my $cl = &$tcp_connect;
$conf{SSL_ocsp_mode} |= SSL_OCSP_FULL_CHAIN;
if ( ! IO::Socket::SSL->start_SSL($cl, %conf)) {
die sprintf("failed with SSL_ocsp_mode=%b, even though it succeeded with default mode",
$conf{SSL_ocsp_mode});
}
my $ocsp_resolver = $cl->ocsp_resolver;
my %todo = $ocsp_resolver->requests;
while (my ($uri,$req) = each %todo) {
VERBOSE(3,"need to send %d bytes OCSP request to %s",length($req),$uri);
}
my $errors = $ocsp_resolver->resolve_blocking();
die "resolver not finished " if ! defined $errors;
if ( ! $errors ) {
VERBOSE(1,"all certificates verified");
$ocsp_status = "good";
} else {
VERBOSE(1,"failed to verify certicates: $errors");
$ocsp_status = "FAIL: $errors";
}
if (my $soft_error = $ocsp_resolver->soft_error) {
$ocsp_status .= " (soft error: $soft_error)"
}
}
# check out all supported ciphers
my @ciphers;
{
my $c = 'HIGH:ALL:eNULL';
while ($all_ciphers || @ciphers<2 ) {
my $cl = &$tcp_connect;
if ( IO::Socket::SSL->start_SSL($cl,
SSL_verify_mode => 0,
SSL_version => $conf{SSL_version},
SSL_cipher_list => $c,
)) {
push @ciphers, [ $cl->get_sslversion, $cl->get_cipher ];
$c .= ":!".$ciphers[-1][1];
VERBOSE(2,"connect with version %s cipher %s",
@{$ciphers[-1]});
} else {
VERBOSE(3,"handshake failed with $c: $SSL_ERROR");
last;
}
}
}
# try to detect if the server accepts our cipher order by trying two
# ciphers in different order
my $server_cipher_order;
if (@ciphers>=2) {
my %used_cipher;
for( "$ciphers[0][1]:$ciphers[1][1]","$ciphers[1][1]:$ciphers[0][1]" ) {
my $cl = &$tcp_connect;
if ( IO::Socket::SSL->start_SSL($cl,
SSL_version => $use_version,
SSL_verify_mode => 0,
SSL_hostname => '',
SSL_cipher_list => $_,
)) {
$used_cipher{$cl->get_cipher}++;
} else {
warn "failed to SSL handshake with SSL_cipher_list=$_: $SSL_ERROR";
}
}
if (keys(%used_cipher) == 2) {
VERBOSE(2,"client decides cipher order");
$server_cipher_order = 0;
} elsif ( (values(%used_cipher))[0] == 2 ) {
VERBOSE(2,"server decides cipher order");
$server_cipher_order = 1;
}
}
# summary
print "-- $host port $port".($stls? " starttls $stls":"")."\n";
print " ! $_\n" for(@problems);
print " * maximum SSL version : $version ($use_version)\n";
print " * preferred cipher : $cipher\n";
print " * cipher order by : ".(
! defined $server_cipher_order ? "unknown\n" :
$server_cipher_order ? "server\n" : "client\n"
);
print " * SNI supported : $sni_status\n" if $sni_status;
print " * certificate verified : $verify_status\n";
if ($show_chain) {
for(my $i=0;$i<@cert_chain;$i++) {
my $c = $cert_chain[$i];
print " * [$i] bits=$c->[0], ocsp_uri=$c->[2], $c->[1]\n"
}
if (@cert_chain_nosni) {
print " * chain without SNI\n";
for(my $i=0;$i<@cert_chain_nosni;$i++) {
my $c = $cert_chain_nosni[$i];
print " * [$i] bits=$c->[0], ocsp_uri=$c->[2], $c->[1]\n"
}
}
}
print " * OCSP stapling : $ocsp_staple\n" if $ocsp_staple;
print " * OCSP status : $ocsp_status\n" if $ocsp_status;
if ($all_ciphers) {
print " * supported ciphers\n";
for(@ciphers) {
printf " * %6s %s\n",@$_;
}
}
if ($dump_chain) {
print "---------------------------------------------------------------\n";
for(my $i=0;$i<@cert_chain;$i++) {
my $c = $cert_chain[$i];
print "# $c->[1]\n$c->[3]\n";
}
}
}
sub smtp_starttls {
my $cl = $ioclass->new(%{shift()}) or die "tcp connect: $!";
my $last_status_line = qr/((\d)\d\d(?:\s.*)?)/;
my ($line,$code) = _readlines($cl,$last_status_line);
$code == 2 or die "server denies access: $line\n";
print $cl "EHLO example.com\r\n";
($line,$code) = _readlines($cl,$last_status_line);
$code == 2 or die "server did not accept EHLO: $line\n";
print $cl "STARTTLS\r\n";
($line,$code) = _readlines($cl,$last_status_line);
$code == 2 or die "server did not accept STARTTLS: $line\n";
VERBOSE(3,"...reply to starttls: $line");
return $cl;
}
sub imap_starttls {
my $cl = $ioclass->new(%{shift()}) or die "tcp connect: $!";
<$cl>; # welcome
print $cl "abc STARTTLS\r\n";
while (<$cl>) {
m{^abc (OK)?} or next;
$1 or die "STARTTLS failed: $_";
s{\r?\n$}{};
VERBOSE(3,"...starttls: $_");
return $cl;
}
die "starttls failed";
}
sub pop_stls {
my $cl = $ioclass->new(%{shift()}) or die "tcp connect: $!";
<$cl>; # welcome
print $cl "STLS\r\n";
my $reply = <$cl>;
die "STLS failed: $reply" if $reply !~m{^\+OK};
$reply =~s{\r?\n}{};
VERBOSE(3,"...stls $reply");
return $cl;
}
sub http_connect {
my ($ioargs,$proxy) = @_;
$proxy or die "no proxy host:port given";
$proxy =~m{^(?:\[(.+)\]|([^:]+)):(\w+)$} or die "invalid dst: $proxy";
my $cl = $ioclass->new( %$ioargs,
PeerAddr => $1||$2,
PeerPort => $3,
) or die "tcp connect: $!";
print $cl "CONNECT $ioargs->{PeerAddr}:$ioargs->{PeerPort} HTTP/1.0\r\n\r\n";
my $hdr = _readlines($cl,qr/\r?\n/);
$hdr =~m{\A(HTTP/1\.[01]\s+(\d\d\d)[^\r\n]*)};
die "CONNECT failed: $1" if $2 != 200;
VERBOSE(3,"...connect request: $1");
return $cl;
}
sub http_upgrade {
my ($ioargs,$arg) = @_;
my $hostname = $ioargs->{PeerAddr};
my $cl = $ioclass->new(%$ioargs) or die "tcp connect: $!";
my $rq;
if ( $arg && $arg =~m{^get(?:=(\S+))?}i ) {
my $path = $1 || '/';
$rq = "GET $path HTTP/1.1\r\n".
"Host: $hostname\r\n".
"Upgrade: TLS/1.0\r\n".
"Connection: Upgrade\r\n".
"\r\n";
} else {
my $path = $arg && $arg =~m{^options=(\S+)}i
? $1:'*';
$rq = "OPTIONS $path HTTP/1.1\r\n".
"Host: $hostname\r\n".
"Upgrade: TLS/1.0\r\n".
"Connection: Upgrade\r\n".
"\r\n";
}
print $cl $rq;
my $hdr = _readlines($cl,qr/\r?\n/);
$hdr =~m{\A(HTTP/1\.[01]\s+(\d\d\d)[^\r\n]*)};
die "upgrade not accepted, code=$2 (expect 101): $1" if $2 != 101;
VERBOSE(3,"...tls upgrade request: $1");
return $cl;
}
sub ftp_auth {
my $cl = $ioclass->new(%{shift()}) or die "tcp connect: $!";
my $last_status_line = qr/((\d)\d\d(?:\s.*)?)/;
my ($line,$code) = _readlines($cl,$last_status_line);
die "server denies access: $line\n" if $code != 2;
print $cl "AUTH TLS\r\n";
($line,$code) = _readlines($cl,$last_status_line);
die "AUTH TLS denied: $line\n" if $code != 2;
VERBOSE(3,"...ftp auth: $line");
return $cl;
}
sub postgresql_init {
my $cl = $ioclass->new(%{shift()}) or die "tcp connect: $!";
# magic header to initiate SSL:
# http://www.postgresql.org/docs/devel/static/protocol-message-formats.html
print $cl pack("NN",8,80877103);
read($cl, my $buf,1 ) or die "did not get response from postgresql";
$buf eq 'S' or die "postgresql does not support SSL (response=$buf)";
VERBOSE(3,"...postgresql supports SSL: $buf");
return $cl;
}
sub _readlines {
my ($cl,$stoprx) = @_;
my $buf = '';
while (<$cl>) {
$buf .= $_;
return $buf if ! $stoprx;
next if ! m{\A$stoprx\Z};
return ( m{\A$stoprx\Z},$buf );
}
die "eof" if $buf eq '';
die "unexpected response: $buf";
}
sub VERBOSE {
my $level = shift;
$verbose>=$level || return;
my $msg = shift;
$msg = sprintf($msg,@_) if @_;
my $prefix = $level == 1 ? '+ ' : $level == 2 ? '* ' : "<$level> ";
print STDERR "$prefix$msg\n";
}