diff --git a/highlighters/main/test-data/exec-redirection1.zsh b/highlighters/main/test-data/exec-redirection1.zsh
new file mode 100644
index 0000000..880cfea
--- /dev/null
+++ b/highlighters/main/test-data/exec-redirection1.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
+# -------------------------------------------------------------------------------------------------
+
+ZSH_HIGHLIGHT_STYLES[redirection]=$unused_highlight
+BUFFER='exec {foo}>&/tmp ls'
+
+expected_region_highlight=(
+  "1 4 $ZSH_HIGHLIGHT_STYLES[precommand]" # exec
+  # TODO: "6 10 $ZSH_HIGHLIGHT_STYLES[redirection] 'issue #238'" # {foo}
+  "11 12 $ZSH_HIGHLIGHT_STYLES[redirection]" # >&
+  "13 16 $ZSH_HIGHLIGHT_STYLES[path]" # /tmp
+  "18 19 $ZSH_HIGHLIGHT_STYLES[command] 'issue #238'" # ls
+)
diff --git a/highlighters/main/test-data/sudo-redirection3.zsh b/highlighters/main/test-data/sudo-redirection3.zsh
new file mode 100644
index 0000000..f885d9f
--- /dev/null
+++ b/highlighters/main/test-data/sudo-redirection3.zsh
@@ -0,0 +1,40 @@
+# -------------------------------------------------------------------------------------------------
+# 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
+# -------------------------------------------------------------------------------------------------
+
+ZSH_HIGHLIGHT_STYLES[redirection]=$unused_highlight
+BUFFER='sudo 2>./. -u otheruser ls'
+
+expected_region_highlight=(
+  "1 4 $ZSH_HIGHLIGHT_STYLES[precommand]" # sudo
+  "6 7 $ZSH_HIGHLIGHT_STYLES[redirection] 'issue #238'" # 2>
+  "8 10 $ZSH_HIGHLIGHT_STYLES[path]" # ./. # a 3-character path, for alignment with sudo-redirection2.zsh
+  "12 13 $ZSH_HIGHLIGHT_STYLES[single-hyphen-option]" # -u
+  "15 23 $ZSH_HIGHLIGHT_STYLES[default]" # otheruser
+  "25 26 $ZSH_HIGHLIGHT_STYLES[command] 'issue #238'" # ls
+)