diff --git a/t/Email/set/.destroy.t.swp b/t/Email/set/.destroy.t.swp
deleted file mode 100644
index d81b3d4..0000000
Binary files a/t/Email/set/.destroy.t.swp and /dev/null differ
diff --git a/t/Email/set/update.t b/t/Email/set/update.t
new file mode 100644
index 0000000..8019865
--- /dev/null
+++ b/t/Email/set/update.t
@@ -0,0 +1,119 @@
+use strict;
+use warnings;
+use Test::Routine;
+use Test::Routine::Util;
+
+with 'JMAP::TestSuite::Tester';
+
+use JMAP::TestSuite::Util qw(batch_ok pristine_test);
+
+use Test::Deep ':v1';
+use Test::Deep::JType;
+use Test::More;
+use JSON qw(decode_json);
+use JSON::Typist;
+use Test::Abortable;
+use Path::Tiny;
+use Digest::MD5 qw(md5_hex);
+
+use utf8;
+
+test "update email keywords" => sub {
+  my ($self) = @_;
+
+  my $tester = $self->tester;
+
+  my $mbox = $self->context->create_mailbox;
+
+  my $from    = "test$$\@example.net";
+  my $to      = "recip$$\@example.net";
+  my $subject = "A subject for $$";
+ 
+  my @setters = (
+    {
+      desc  => "bulk set",
+      data  => { keywords => { '$Flagged' => jtrue } },
+    },
+    {
+      desc  => "patch set",
+      data  => { 'keywords/$Flagged' => jtrue },
+    },
+    {
+      desc  => "patch set integer",
+      data  => { 'keywords/$Flagged' => 1 },
+      fail  => 1,
+    },
+  );
+
+  my @clearers = (
+    {
+      desc  => "bulk clear",
+      data => { keywords => { } },
+    },
+    {
+      desc  => "patch set null",
+      data  => { 'keywords/$Flagged' => undef },
+    },
+    {
+      desc  => "patch set false",
+      data  => { 'keywords/$Flagged' => jfalse },
+      set_fail => 1,
+    },
+  );
+  
+  SETTER: for my $setter (@setters) {
+    GETTER: for my $clearer (@clearers) {
+      subtest "setter($setter->{desc}) clearer($clearer->{desc})" => sub {
+        my $message = $mbox->add_message({
+          from    => $from,
+          to      => $to,
+          subject => $subject,
+        });
+
+        $tester->request_ok(
+          [ "Email/get" => { ids => [ $message->id ] } ],
+          superhashof({ list => [ superhashof({ keywords => {} }) ] }),
+          "newly created email has no keywords",
+        );
+
+        $tester->request_ok(
+          [ "Email/set" => { update => { $message->id => $setter->{data} } } ],
+          ($setter->{fail}
+            ? superhashof({ notUpdated => { $message->id => ignore } })
+            : superhashof({ updated    => { $message->id => ignore } })),
+          'tried to set $flagged keyword: should ' . ($setter->{fail} ? 'fail' : 'work')
+        );
+
+        return if $setter->{fail};
+
+        $tester->request_ok(
+          [ "Email/get" => { ids => [ $message->id ] } ],
+          superhashof({ list => [ superhashof({ keywords => { '$flagged' => jtrue() } }) ] }),
+          '...and it worked, keyword $flagged set',
+        );
+
+        $tester->request_ok(
+          [ "Email/set" => { update => { $message->id => $clearer->{data} } } ],
+          ($clearer->{fail}
+            ? superhashof({ notUpdated => { $message->id => ignore } })
+            : superhashof({ updated    => { $message->id => ignore } })),
+          'tried to clear $flagged keyword: should ' . ($clearer->{fail} ? 'fail' : 'work')
+        );
+
+        return if $clearer->{fail};
+
+        $tester->request_ok(
+          [ "Email/get" => { ids => [ $message->id ] } ],
+          superhashof({ list => [ superhashof({ keywords => { } }) ] }),
+          "...and it worked, keyword removed",
+        );
+      };
+
+      next SETTER if $setter->{fail};
+    }
+  }
+};
+
+run_me;
+done_testing;
+