diff --git a/highlighters/main/main-highlighter.zsh b/highlighters/main/main-highlighter.zsh
index b11b8f1..27ddb0c 100644
--- a/highlighters/main/main-highlighter.zsh
+++ b/highlighters/main/main-highlighter.zsh
@@ -406,6 +406,8 @@ _zsh_highlight_main_highlighter_highlight_list()
   # - :regular:    "Not a command word", and command delimiters are permitted.
   #                Mainly used to detect premature termination of commands.
   # - :always:     The word 'always' in the «{ foo } always { bar }» syntax.
+  # - :test:       Between [[ and ]]
+  # - :end:        Must be a command separator; anything else is a syntax error.
   #
   # When the kind of a word is not yet known, $this_word / $next_word may contain
   # multiple states.  For example, after "sudo -i", the next word may be either
@@ -650,11 +652,26 @@ _zsh_highlight_main_highlighter_highlight_list()
    fi
 
    # The Great Fork: is this a command word?  Is this a non-command word?
-   if [[ -n ${(M)ZSH_HIGHLIGHT_TOKENS_COMMANDSEPARATOR:#"$arg"} ]]; then
+   if [[ $this_word == :test: ]]; then
+     next_word=:test:
+     if [[ $arg == $'\x5d\x5d' ]]; then
+       _zsh_highlight_main__stack_pop T reserved-word
+       next_word=:end:
+     elif [[ $arg == ('&&'|'||') ]]; then
+       style=reserved-word
+     elif [[ -n ${(M)ZSH_HIGHLIGHT_TOKENS_COMMANDSEPARATOR:#"$arg"} ]]; then
+       style=unknown-token
+       next_word=:start:
+       highlight_glob=true
+     else
+       _zsh_highlight_main_highlighter_highlight_argument 1 1
+       continue
+     fi
+   elif [[ -n ${(M)ZSH_HIGHLIGHT_TOKENS_COMMANDSEPARATOR:#"$arg"} ]]; then
      if _zsh_highlight_main__stack_pop T || _zsh_highlight_main__stack_pop Q; then
        # Missing closing square bracket(s)
        style=unknown-token
-     elif [[ $this_word == *':regular:'* ]]; then
+     elif [[ $this_word == *':regular:'* || $this_word == *:end:* ]]; then
        # This highlights empty commands (semicolon follows nothing) as an error.
        # Zsh accepts them, though.
        style=commandseparator
@@ -668,6 +685,8 @@ _zsh_highlight_main_highlighter_highlight_list()
        next_word=':start:'
        highlight_glob=true
      fi
+   elif [[ $this_word == *:end:* ]]; then
+     style=unknown-token
    elif ! (( in_redirection)) && [[ $this_word == *':always:'* && $arg == 'always' ]]; then
      # try-always construct
      style=reserved-word # de facto a reserved word, although not de jure
@@ -699,6 +718,7 @@ _zsh_highlight_main_highlighter_highlight_list()
                             ;;
                           ($'\x5b\x5b')
                             braces_stack='T'"$braces_stack"
+			    next_word=:test:
                             ;;
                           ('do')
                             braces_stack='D'"$braces_stack"
@@ -868,8 +888,6 @@ _zsh_highlight_main_highlighter_highlight_list()
                    fi
                  elif [[ $arg[0,1] = $histchars[0,1] ]] && (( $#arg[0,2] == 2 )); then
                    style=history-expansion
-                 elif [[ $arg == $'\x5d\x5d' ]] && _zsh_highlight_main__stack_pop 'T' reserved-word; then
-                   :
                  elif [[ $arg == $'\x5d' ]] && _zsh_highlight_main__stack_pop 'Q' builtin; then
                    :
                  else
diff --git a/highlighters/main/test-data/test-trailing1.zsh b/highlighters/main/test-data/test-trailing1.zsh
new file mode 100644
index 0000000..2dbd110
--- /dev/null
+++ b/highlighters/main/test-data/test-trailing1.zsh
@@ -0,0 +1,39 @@
+#!/usr/bin/env zsh
+# -------------------------------------------------------------------------------------------------
+# Copyright (c) 2018 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='[[ -n $foo ]] echo'
+
+expected_region_highlight=(
+  '1 2 reserved-word' # [[
+  '4 5 single-hyphen-option' # -n
+  '7 10 default' # $foo
+  '12 13 reserved-word' # ]]
+  '15 18 unknown-token' # echo
+)
diff --git a/highlighters/main/test-data/test-trailing2.zsh b/highlighters/main/test-data/test-trailing2.zsh
new file mode 100644
index 0000000..9204bf0
--- /dev/null
+++ b/highlighters/main/test-data/test-trailing2.zsh
@@ -0,0 +1,40 @@
+#!/usr/bin/env zsh
+# -------------------------------------------------------------------------------------------------
+# Copyright (c) 2018 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='[[ -n $foo ]] | echo'
+
+expected_region_highlight=(
+  '1 2 reserved-word' # [[
+  '4 5 single-hyphen-option' # -n
+  '7 10 default' # $foo
+  '12 13 reserved-word' # ]]
+  '15 15 commandseparator' # |
+  '17 20 builtin' # echo
+)
diff --git a/highlighters/main/test-data/test1.zsh b/highlighters/main/test-data/test1.zsh
new file mode 100644
index 0000000..93d1bcf
--- /dev/null
+++ b/highlighters/main/test-data/test1.zsh
@@ -0,0 +1,41 @@
+#!/usr/bin/env zsh
+# -------------------------------------------------------------------------------------------------
+# Copyright (c) 2018 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='[[ -n $foo || -z $bar ]]'
+
+expected_region_highlight=(
+  '1 2 reserved-word' # [[
+  '4 5 single-hyphen-option' # -n
+  '7 10 default' # $foo
+  '12 13 reserved-word' # ||
+  '15 16 single-hyphen-option' # -z
+  '18 21 default' # $bar
+  '23 24 reserved-word' # ]]
+)
diff --git a/highlighters/main/test-data/test2.zsh b/highlighters/main/test-data/test2.zsh
new file mode 100644
index 0000000..ab3b96f
--- /dev/null
+++ b/highlighters/main/test-data/test2.zsh
@@ -0,0 +1,41 @@
+#!/usr/bin/env zsh
+# -------------------------------------------------------------------------------------------------
+# Copyright (c) 2018 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='[[ -n $foo && -z $bar ]]'
+
+expected_region_highlight=(
+  '1 2 reserved-word' # [[
+  '4 5 single-hyphen-option' # -n
+  '7 10 default' # $foo
+  '12 13 reserved-word' # &&
+  '15 16 single-hyphen-option' # -z
+  '18 21 default' # $bar
+  '23 24 reserved-word' # ]]
+)