diff --git a/mercurial/mail.py b/mercurial/mail.py
--- a/mercurial/mail.py
+++ b/mercurial/mail.py
@@ -152,7 +152,8 @@ def _smtp(ui):
 def _sendmail(ui, sender, recipients, msg):
     '''send mail using sendmail.'''
     program = ui.config('email', 'method')
-    stremail = lambda x: stringutil.email(encoding.strtolocal(x))
+    stremail = lambda x: (
+        procutil.quote(stringutil.email(encoding.strtolocal(x))))
     cmdline = '%s -f %s %s' % (program, stremail(sender),
                                ' '.join(map(stremail, recipients)))
     ui.note(_('sending mail: %s\n') % cmdline)
diff --git a/mercurial/pycompat.py b/mercurial/pycompat.py
--- a/mercurial/pycompat.py
+++ b/mercurial/pycompat.py
@@ -328,8 +328,11 @@ if ispy3:
         ret = shlex.split(s.decode('latin-1'), comments, posix)
         return [a.encode('latin-1') for a in ret]
 
+    shlexquote = shlex.quote
+
 else:
     import cStringIO
+    import pipes
 
     xrange = xrange
     unicode = unicode
@@ -393,6 +396,7 @@ else:
     sysplatform = sys.platform
     sysexecutable = sys.executable
     shlexsplit = shlex.split
+    shlexquote = pipes.quote
     bytesio = cStringIO.StringIO
     stringio = bytesio
     maplist = map
diff --git a/mercurial/utils/procutil.py b/mercurial/utils/procutil.py
--- a/mercurial/utils/procutil.py
+++ b/mercurial/utils/procutil.py
@@ -70,6 +70,7 @@ shellsplit = platform.shellsplit
 spawndetached = platform.spawndetached
 sshargs = platform.sshargs
 testpid = platform.testpid
+quote = pycompat.shlexquote
 
 try:
     setprocname = osutil.setprocname
diff --git a/tests/test-patchbomb.t b/tests/test-patchbomb.t
--- a/tests/test-patchbomb.t
+++ b/tests/test-patchbomb.t
@@ -3035,6 +3035,47 @@ single rev
   sending [PATCH] test ...
   sending mail: $TESTTMP/t2/pretendmail.sh -f test foo
 
+Shell characters in addresses
+
+  $ hg email --date '1980-1-1 0:1' -v -t '~foo/bar@example.com' -f 'me*@example.com' -r '10'
+  this patch series consists of 1 patches.
+  
+  warning: invalid patchbomb.intro value "mpmwearaclownnose"
+  (should be one of always, never, auto)
+  -f me*@example.com ~foo/bar@example.com
+  MIME-Version: 1.0
+  Content-Type: text/plain; charset="us-ascii"
+  Content-Transfer-Encoding: 7bit
+  Subject: [PATCH] dd
+  X-Mercurial-Node: 3b6f1ec9dde933a40a115a7990f8b320477231af
+  X-Mercurial-Series-Index: 1
+  X-Mercurial-Series-Total: 1
+  Message-Id: <3b6f1ec9dde933a40a11.315532860@test-hostname>
+  X-Mercurial-Series-Id: <3b6f1ec9dde933a40a11.315532860@test-hostname>
+  User-Agent: Mercurial-patchbomb/* (glob)
+  Date: Tue, 01 Jan 1980 00:01:00 +0000
+  From: me*@example.com
+  To: ~foo/bar@example.com
+  
+  # HG changeset patch
+  # User test
+  # Date 5 0
+  #      Thu Jan 01 00:00:05 1970 +0000
+  # Branch test
+  # Node ID 3b6f1ec9dde933a40a115a7990f8b320477231af
+  # Parent  2f9fa9b998c5fe3ac2bd9a2b14bfcbeecbc7c268
+  dd
+  
+  diff -r 2f9fa9b998c5 -r 3b6f1ec9dde9 d
+  --- a/d	Thu Jan 01 00:00:04 1970 +0000
+  +++ b/d	Thu Jan 01 00:00:05 1970 +0000
+  @@ -1,1 +1,2 @@
+   d
+  +d
+  
+  sending [PATCH] dd ...
+  sending mail: $TESTTMP/t2/pretendmail.sh -f 'me*@example.com' '~foo/bar@example.com'
+
 Test pull url header
 =================================