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diff --git a/rt/t/web/gnupg-select-keys-on-update.t b/rt/t/web/gnupg-select-keys-on-update.t
new file mode 100644
index 000000000..76817ddf2
--- /dev/null
+++ b/rt/t/web/gnupg-select-keys-on-update.t
@@ -0,0 +1,344 @@
+#!/usr/bin/perl -w
+use strict;
+use warnings;
+
+use RT::Test tests => 68;
+
+plan skip_all => 'GnuPG required.'
+    unless eval 'use GnuPG::Interface; 1';
+plan skip_all => 'gpg executable is required.'
+    unless RT::Test->find_executable('gpg');
+
+
+use RT::Action::SendEmail;
+use File::Temp qw(tempdir);
+
+RT::Test->set_mail_catcher;
+
+use_ok('RT::Crypt::GnuPG');
+
+RT->Config->Set( GnuPG =>
+    Enable => 1,
+    OutgoingMessagesFormat => 'RFC',
+);
+
+RT->Config->Set( GnuPGOptions =>
+    homedir => scalar tempdir( CLEANUP => 0 ),
+    passphrase => 'rt-test',
+    'no-permission-warning' => undef,
+);
+diag "GnuPG --homedir ". RT->Config->Get('GnuPGOptions')->{'homedir'} if $ENV{TEST_VERBOSE};
+
+RT->Config->Set( 'MailPlugins' => 'Auth::MailFrom', 'Auth::GnuPG' );
+
+my $queue = RT::Test->load_or_create_queue(
+    Name              => 'Regression',
+    CorrespondAddress => 'rt-recipient@example.com',
+    CommentAddress    => 'rt-recipient@example.com',
+);
+ok $queue && $queue->id, 'loaded or created queue';
+
+RT::Test->set_rights(
+    Principal => 'Everyone',
+    Right => ['CreateTicket', 'ShowTicket', 'SeeQueue', 'ReplyToTicket', 'ModifyTicket'],
+);
+
+my ($baseurl, $m) = RT::Test->started_ok;
+ok $m->login, 'logged in';
+
+
+my $tid;
+{
+    my $ticket = RT::Ticket->new( $RT::SystemUser );
+    ($tid) = $ticket->Create(
+        Subject   => 'test',
+        Queue     => $queue->id,
+    );
+    ok $tid, 'ticket created';
+}
+
+diag "check that signing doesn't work if there is no key" if $ENV{TEST_VERBOSE};
+{
+    RT::Test->clean_caught_mails;
+
+    ok $m->goto_ticket( $tid ), "UI -> ticket #$tid";
+    $m->follow_link_ok( { text => 'Reply' }, 'ticket -> reply' );
+    $m->form_number(3);
+    $m->tick( Sign => 1 );
+    $m->field( UpdateCc => 'rt-test@example.com' );
+    $m->field( UpdateContent => 'Some content' );
+    $m->click('SubmitTicket');
+    $m->content_like(
+        qr/unable to sign outgoing email messages/i,
+        'problems with passphrase'
+    );
+
+    my @mail = RT::Test->fetch_caught_mails;
+    ok !@mail, 'there are no outgoing emails';
+}
+
+{
+    RT::Test->import_gnupg_key('rt-recipient@example.com');
+    RT::Test->trust_gnupg_key('rt-recipient@example.com');
+    my %res = RT::Crypt::GnuPG::GetKeysInfo('rt-recipient@example.com');
+    is $res{'info'}[0]{'TrustTerse'}, 'ultimate', 'ultimately trusted key';
+}
+
+diag "check that things don't work if there is no key" if $ENV{TEST_VERBOSE};
+{
+    RT::Test->clean_caught_mails;
+
+    ok $m->goto_ticket( $tid ), "UI -> ticket #$tid";
+    $m->follow_link_ok( { text => 'Reply' }, 'ticket -> reply' );
+    $m->form_number(3);
+    $m->tick( Encrypt => 1 );
+    $m->field( UpdateCc => 'rt-test@example.com' );
+    $m->field( UpdateContent => 'Some content' );
+    $m->click('SubmitTicket');
+    $m->content_like(
+        qr/You are going to encrypt outgoing email messages/i,
+        'problems with keys'
+    );
+    $m->content_like(
+        qr/There is no key suitable for encryption/i,
+        'problems with keys'
+    );
+
+    my $form = $m->form_number(3);
+    ok !$form->find_input( 'UseKey-rt-test@example.com' ), 'no key selector';
+
+    my @mail = RT::Test->fetch_caught_mails;
+    ok !@mail, 'there are no outgoing emails';
+}
+
+
+diag "import first key of rt-test\@example.com" if $ENV{TEST_VERBOSE};
+my $fpr1 = '';
+{
+    RT::Test->import_gnupg_key('rt-test@example.com', 'public');
+    my %res = RT::Crypt::GnuPG::GetKeysInfo('rt-test@example.com');
+    is $res{'info'}[0]{'TrustLevel'}, 0, 'is not trusted key';
+    $fpr1 = $res{'info'}[0]{'Fingerprint'};
+}
+
+diag "check that things still doesn't work if key is not trusted" if $ENV{TEST_VERBOSE};
+{
+    RT::Test->clean_caught_mails;
+
+    ok $m->goto_ticket( $tid ), "UI -> ticket #$tid";
+    $m->follow_link_ok( { text => 'Reply' }, 'ticket -> reply' );
+    $m->form_number(3);
+    $m->tick( Encrypt => 1 );
+    $m->field( UpdateCc => 'rt-test@example.com' );
+    $m->field( UpdateContent => 'Some content' );
+    $m->click('SubmitTicket');
+    $m->content_like(
+        qr/You are going to encrypt outgoing email messages/i,
+        'problems with keys'
+    );
+    $m->content_like(
+        qr/There is one suitable key, but trust level is not set/i,
+        'problems with keys'
+    );
+
+    my $form = $m->form_number(3);
+    ok my $input = $form->find_input( 'UseKey-rt-test@example.com' ), 'found key selector';
+    is scalar $input->possible_values, 1, 'one option';
+
+    $m->select( 'UseKey-rt-test@example.com' => $fpr1 );
+    $m->click('SubmitTicket');
+    $m->content_like(
+        qr/You are going to encrypt outgoing email messages/i,
+        'problems with keys'
+    );
+    $m->content_like(
+        qr/Selected key either is not trusted/i,
+        'problems with keys'
+    );
+
+    my @mail = RT::Test->fetch_caught_mails;
+    ok !@mail, 'there are no outgoing emails';
+}
+
+diag "import a second key of rt-test\@example.com" if $ENV{TEST_VERBOSE};
+my $fpr2 = '';
+{
+    RT::Test->import_gnupg_key('rt-test@example.com.2', 'public');
+    my %res = RT::Crypt::GnuPG::GetKeysInfo('rt-test@example.com');
+    is $res{'info'}[1]{'TrustLevel'}, 0, 'is not trusted key';
+    $fpr2 = $res{'info'}[2]{'Fingerprint'};
+}
+
+diag "check that things still doesn't work if two keys are not trusted" if $ENV{TEST_VERBOSE};
+{
+    RT::Test->clean_caught_mails;
+
+    ok $m->goto_ticket( $tid ), "UI -> ticket #$tid";
+    $m->follow_link_ok( { text => 'Reply' }, 'ticket -> reply' );
+    $m->form_number(3);
+    $m->tick( Encrypt => 1 );
+    $m->field( UpdateCc => 'rt-test@example.com' );
+    $m->field( UpdateContent => 'Some content' );
+    $m->click('SubmitTicket');
+    $m->content_like(
+        qr/You are going to encrypt outgoing email messages/i,
+        'problems with keys'
+    );
+    $m->content_like(
+        qr/There are several keys suitable for encryption/i,
+        'problems with keys'
+    );
+
+    my $form = $m->form_number(3);
+    ok my $input = $form->find_input( 'UseKey-rt-test@example.com' ), 'found key selector';
+    is scalar $input->possible_values, 2, 'two options';
+
+    $m->select( 'UseKey-rt-test@example.com' => $fpr1 );
+    $m->click('SubmitTicket');
+    $m->content_like(
+        qr/You are going to encrypt outgoing email messages/i,
+        'problems with keys'
+    );
+    $m->content_like(
+        qr/Selected key either is not trusted/i,
+        'problems with keys'
+    );
+
+    my @mail = RT::Test->fetch_caught_mails;
+    ok !@mail, 'there are no outgoing emails';
+}
+
+{
+    RT::Test->lsign_gnupg_key( $fpr1 );
+    my %res = RT::Crypt::GnuPG::GetKeysInfo('rt-test@example.com');
+    ok $res{'info'}[0]{'TrustLevel'} > 0, 'trusted key';
+    is $res{'info'}[1]{'TrustLevel'}, 0, 'is not trusted key';
+}
+
+diag "check that we see key selector even if only one key is trusted but there are more keys" if $ENV{TEST_VERBOSE};
+{
+    RT::Test->clean_caught_mails;
+
+    ok $m->goto_ticket( $tid ), "UI -> ticket #$tid";
+    $m->follow_link_ok( { text => 'Reply' }, 'ticket -> reply' );
+    $m->form_number(3);
+    $m->tick( Encrypt => 1 );
+    $m->field( UpdateCc => 'rt-test@example.com' );
+    $m->field( UpdateContent => 'Some content' );
+    $m->click('SubmitTicket');
+    $m->content_like(
+        qr/You are going to encrypt outgoing email messages/i,
+        'problems with keys'
+    );
+    $m->content_like(
+        qr/There are several keys suitable for encryption/i,
+        'problems with keys'
+    );
+
+    my $form = $m->form_number(3);
+    ok my $input = $form->find_input( 'UseKey-rt-test@example.com' ), 'found key selector';
+    is scalar $input->possible_values, 2, 'two options';
+
+    my @mail = RT::Test->fetch_caught_mails;
+    ok !@mail, 'there are no outgoing emails';
+}
+
+diag "check that key selector works and we can select trusted key" if $ENV{TEST_VERBOSE};
+{
+    RT::Test->clean_caught_mails;
+
+    ok $m->goto_ticket( $tid ), "UI -> ticket #$tid";
+    $m->follow_link_ok( { text => 'Reply' }, 'ticket -> reply' );
+    $m->form_number(3);
+    $m->tick( Encrypt => 1 );
+    $m->field( UpdateCc => 'rt-test@example.com' );
+    $m->field( UpdateContent => 'Some content' );
+    $m->click('SubmitTicket');
+    $m->content_like(
+        qr/You are going to encrypt outgoing email messages/i,
+        'problems with keys'
+    );
+    $m->content_like(
+        qr/There are several keys suitable for encryption/i,
+        'problems with keys'
+    );
+
+    my $form = $m->form_number(3);
+    ok my $input = $form->find_input( 'UseKey-rt-test@example.com' ), 'found key selector';
+    is scalar $input->possible_values, 2, 'two options';
+
+    $m->select( 'UseKey-rt-test@example.com' => $fpr1 );
+    $m->click('SubmitTicket');
+    $m->content_like( qr/Message recorded/i, 'Message recorded' );
+
+    my @mail = RT::Test->fetch_caught_mails;
+    ok @mail, 'there are some emails';
+    check_text_emails( { Encrypt => 1 }, @mail );
+}
+
+diag "check encrypting of attachments" if $ENV{TEST_VERBOSE};
+{
+    RT::Test->clean_caught_mails;
+
+    ok $m->goto_ticket( $tid ), "UI -> ticket #$tid";
+    $m->follow_link_ok( { text => 'Reply' }, 'ticket -> reply' );
+    $m->form_number(3);
+    $m->tick( Encrypt => 1 );
+    $m->field( UpdateCc => 'rt-test@example.com' );
+    $m->field( UpdateContent => 'Some content' );
+    $m->field( Attach => $0 );
+    $m->click('SubmitTicket');
+    $m->content_like(
+        qr/You are going to encrypt outgoing email messages/i,
+        'problems with keys'
+    );
+    $m->content_like(
+        qr/There are several keys suitable for encryption/i,
+        'problems with keys'
+    );
+
+    my $form = $m->form_number(3);
+    ok my $input = $form->find_input( 'UseKey-rt-test@example.com' ), 'found key selector';
+    is scalar $input->possible_values, 2, 'two options';
+
+    $m->select( 'UseKey-rt-test@example.com' => $fpr1 );
+    $m->click('SubmitTicket');
+    $m->content_like( qr/Message recorded/i, 'Message recorded' );
+
+    my @mail = RT::Test->fetch_caught_mails;
+    ok @mail, 'there are some emails';
+    check_text_emails( { Encrypt => 1, Attachment => 1 }, @mail );
+}
+
+sub check_text_emails {
+    my %args = %{ shift @_ };
+    my @mail = @_;
+
+    ok scalar @mail, "got some mail";
+    for my $mail (@mail) {
+        for my $type ('email', 'attachment') {
+            next if $type eq 'attachment' && !$args{'Attachment'};
+
+            my $content = $type eq 'email'
+                        ? "Some content"
+                        : "Attachment content";
+
+            if ( $args{'Encrypt'} ) {
+                unlike $mail, qr/$content/, "outgoing $type was encrypted";
+            } else {
+                like $mail, qr/$content/, "outgoing $type was not encrypted";
+            } 
+
+            next unless $type eq 'email';
+
+            if ( $args{'Sign'} && $args{'Encrypt'} ) {
+                like $mail, qr/BEGIN PGP MESSAGE/, 'outgoing email was signed';
+            } elsif ( $args{'Sign'} ) {
+                like $mail, qr/SIGNATURE/, 'outgoing email was signed';
+            } else {
+                unlike $mail, qr/SIGNATURE/, 'outgoing email was not signed';
+            }
+        }
+    }
+}
+