diff --git a/highlighters/main/test-data/sudo-redirection.zsh b/highlighters/main/test-data/sudo-redirection.zsh
new file mode 100644
index 0000000..bf5a3e7
--- /dev/null
+++ b/highlighters/main/test-data/sudo-redirection.zsh
@@ -0,0 +1,39 @@
+# -------------------------------------------------------------------------------------------------
+# Copyright (c) 2015 zsh-syntax-highlighting contributors
+# All rights reserved.
+#
+# Redistribution and use in source and binary forms, with or without modification, are permitted
+# provided that the following conditions are met:
+#
+#  * Redistributions of source code must retain the above copyright notice, this list of conditions
+#    and the following disclaimer.
+#  * Redistributions in binary form must reproduce the above copyright notice, this list of
+#    conditions and the following disclaimer in the documentation and/or other materials provided
+#    with the distribution.
+#  * Neither the name of the zsh-syntax-highlighting contributors nor the names of its contributors
+#    may be used to endorse or promote products derived from this software without specific prior
+#    written permission.
+#
+# THIS SOFTWARE IS PROVIDED BY THE COPYRIGHT HOLDERS AND CONTRIBUTORS "AS IS" AND ANY EXPRESS OR
+# IMPLIED WARRANTIES, INCLUDING, BUT NOT LIMITED TO, THE IMPLIED WARRANTIES OF MERCHANTABILITY AND
+# FITNESS FOR A PARTICULAR PURPOSE ARE DISCLAIMED. IN NO EVENT SHALL THE COPYRIGHT HOLDER OR
+# CONTRIBUTORS BE LIABLE FOR ANY DIRECT, INDIRECT, INCIDENTAL, SPECIAL, EXEMPLARY, OR CONSEQUENTIAL
+# DAMAGES (INCLUDING, BUT NOT LIMITED TO, PROCUREMENT OF SUBSTITUTE GOODS OR SERVICES; LOSS OF USE,
+# DATA, OR PROFITS; OR BUSINESS INTERRUPTION) HOWEVER CAUSED AND ON ANY THEORY OF LIABILITY, WHETHER
+# IN CONTRACT, STRICT LIABILITY, OR TORT (INCLUDING NEGLIGENCE OR OTHERWISE) ARISING IN ANY WAY OUT
+# OF THE USE OF THIS SOFTWARE, EVEN IF ADVISED OF THE POSSIBILITY OF SUCH DAMAGE.
+# -------------------------------------------------------------------------------------------------
+# -*- mode: zsh; sh-indentation: 2; indent-tabs-mode: nil; sh-basic-offset: 2; -*-
+# vim: ft=zsh sw=2 ts=2 et
+# -------------------------------------------------------------------------------------------------
+
+BUFFER='sudo -u >/tmp otheruser ls'
+
+expected_region_highlight=(
+  "1 4 $ZSH_HIGHLIGHT_STYLES[precommand]" # sudo
+  "6 7 $ZSH_HIGHLIGHT_STYLES[single-hyphen-option]" # -u
+  "9 9 $ZSH_HIGHLIGHT_STYLES[redirection]" # >
+  "10 13 $ZSH_HIGHLIGHT_STYLES[path]" # /tmp
+  "15 23 $ZSH_HIGHLIGHT_STYLES[default]" # otheruser
+  "25 26 $ZSH_HIGHLIGHT_STYLES[command] 'issue #221'" # ls
+)
diff --git a/highlighters/main/test-data/sudo-redirection2.zsh b/highlighters/main/test-data/sudo-redirection2.zsh
new file mode 100644
index 0000000..dcdb8d6
--- /dev/null
+++ b/highlighters/main/test-data/sudo-redirection2.zsh
@@ -0,0 +1,39 @@
+# -------------------------------------------------------------------------------------------------
+# Copyright (c) 2015 zsh-syntax-highlighting contributors
+# All rights reserved.
+#
+# Redistribution and use in source and binary forms, with or without modification, are permitted
+# provided that the following conditions are met:
+#
+#  * Redistributions of source code must retain the above copyright notice, this list of conditions
+#    and the following disclaimer.
+#  * Redistributions in binary form must reproduce the above copyright notice, this list of
+#    conditions and the following disclaimer in the documentation and/or other materials provided
+#    with the distribution.
+#  * Neither the name of the zsh-syntax-highlighting contributors nor the names of its contributors
+#    may be used to endorse or promote products derived from this software without specific prior
+#    written permission.
+#
+# THIS SOFTWARE IS PROVIDED BY THE COPYRIGHT HOLDERS AND CONTRIBUTORS "AS IS" AND ANY EXPRESS OR
+# IMPLIED WARRANTIES, INCLUDING, BUT NOT LIMITED TO, THE IMPLIED WARRANTIES OF MERCHANTABILITY AND
+# FITNESS FOR A PARTICULAR PURPOSE ARE DISCLAIMED. IN NO EVENT SHALL THE COPYRIGHT HOLDER OR
+# CONTRIBUTORS BE LIABLE FOR ANY DIRECT, INDIRECT, INCIDENTAL, SPECIAL, EXEMPLARY, OR CONSEQUENTIAL
+# DAMAGES (INCLUDING, BUT NOT LIMITED TO, PROCUREMENT OF SUBSTITUTE GOODS OR SERVICES; LOSS OF USE,
+# DATA, OR PROFITS; OR BUSINESS INTERRUPTION) HOWEVER CAUSED AND ON ANY THEORY OF LIABILITY, WHETHER
+# IN CONTRACT, STRICT LIABILITY, OR TORT (INCLUDING NEGLIGENCE OR OTHERWISE) ARISING IN ANY WAY OUT
+# OF THE USE OF THIS SOFTWARE, EVEN IF ADVISED OF THE POSSIBILITY OF SUCH DAMAGE.
+# -------------------------------------------------------------------------------------------------
+# -*- mode: zsh; sh-indentation: 2; indent-tabs-mode: nil; sh-basic-offset: 2; -*-
+# vim: ft=zsh sw=2 ts=2 et
+# -------------------------------------------------------------------------------------------------
+
+BUFFER='sudo >/tmp -u otheruser ls'
+
+expected_region_highlight=(
+  "1 4 $ZSH_HIGHLIGHT_STYLES[precommand]" # sudo
+  "6 6 $ZSH_HIGHLIGHT_STYLES[redirection]" # >
+  "7 10 $ZSH_HIGHLIGHT_STYLES[path]" # /tmp
+  "12 13 $ZSH_HIGHLIGHT_STYLES[single-hyphen-option] 'issue #221'" # -u
+  "15 23 $ZSH_HIGHLIGHT_STYLES[default]" # otheruser
+  "25 26 $ZSH_HIGHLIGHT_STYLES[command] 'issue #221'" # ls
+)