diff --git a/highlighters/main/main-highlighter.zsh b/highlighters/main/main-highlighter.zsh
index 5f23357..616d59b 100644
--- a/highlighters/main/main-highlighter.zsh
+++ b/highlighters/main/main-highlighter.zsh
@@ -299,7 +299,7 @@ _zsh_highlight_highlighter_main_paint()
 _zsh_highlight_main_highlighter_highlight_list()
 {
   integer start_pos=0 end_pos buf_offset=$1 has_end=$3
-  local buf=$4 highlight_glob=true arg style
+  local buf=$4 highlight_glob=true arg arg_raw style
   local in_array_assignment=false # true between 'a=(' and the matching ')'
   integer len=$#buf
   local -a match mbegin mend list_highlights
@@ -362,6 +362,9 @@ _zsh_highlight_main_highlighter_highlight_list()
     args=(${(z)buf})
   fi
   for arg in $args; do
+    # Save an unmunged copy of the current word.
+    arg_raw="$arg"
+
     # Initialize $next_word.
     if (( in_redirection )); then
       (( --in_redirection ))
@@ -472,6 +475,30 @@ _zsh_highlight_main_highlighter_highlight_list()
       fi
     fi
 
+    # Expand aliases.
+    # TODO: this should be done iteratively, e.g., 'alias x=y y=z z=w\n x'
+    #       And then the entire 'alias' branch of the 'case' statement should
+    #       be done here.
+    () {
+      # TODO: path expansion should happen _after_ alias expansion
+      _zsh_highlight_main_highlighter_expand_path $arg
+      local expanded_arg="$REPLY"
+      _zsh_highlight_main__type ${expanded_arg}
+    }
+    local res="$REPLY"
+    if [[ $res == "alias" ]]; then
+      _zsh_highlight_main__resolve_alias $arg
+      () {
+        # Use a temporary array to ensure the subscript is interpreted as
+        # an array subscript, not as a scalar subscript
+        local -a reply
+        # TODO: the ${interactive_comments+set} path needs to skip comments; see test-data/alias-comment1.zsh
+        reply=( ${interactive_comments-${(z)REPLY}}
+                ${interactive_comments+${(zZ+c+)REPLY}} )
+        arg=$reply[1]
+      }
+    fi
+
     # Special-case the first word after 'sudo'.
     if (( ! in_redirection )); then
       if [[ $this_word == *':sudo_opt:'* ]] && [[ $arg != -* ]]; then
@@ -512,10 +539,6 @@ _zsh_highlight_main_highlighter_highlight_list()
       next_word+=':sudo_opt:'
       next_word+=':start:'
      else
-      _zsh_highlight_main_highlighter_expand_path $arg
-      local expanded_arg="$REPLY"
-      _zsh_highlight_main__type ${expanded_arg}
-      local res="$REPLY"
       () {
         # Special-case: command word is '$foo', like that, without braces or anything.
         #
@@ -588,8 +611,9 @@ _zsh_highlight_main_highlighter_highlight_list()
                         ;;
         'suffix alias') style=suffix-alias;;
         alias)          () {
+                          # Make sure to use $arg_raw here, rather than $arg.
                           integer insane_alias
-                          case $arg in
+                          case $arg_raw in
                             # Issue #263: aliases with '=' on their LHS.
                             #
                             # There are three cases:
@@ -603,12 +627,13 @@ _zsh_highlight_main_highlighter_highlight_list()
                           esac
                           if (( insane_alias )); then
                             style=unknown-token
+                          # Calling 'type' again; since __type memoizes the answer, this call is just a hash lookup.
+                          elif _zsh_highlight_main__type "$arg"; [[ $REPLY == 'none' ]]; then
+                            style=unknown-token
                           else
                             # The common case.
                             style=alias
-                            _zsh_highlight_main__resolve_alias $arg
-                            local alias_target="$REPLY"
-                            [[ -n ${(M)ZSH_HIGHLIGHT_TOKENS_PRECOMMANDS:#"$alias_target"} && -z ${(M)ZSH_HIGHLIGHT_TOKENS_PRECOMMANDS:#"$arg"} ]] && ZSH_HIGHLIGHT_TOKENS_PRECOMMANDS+=($arg)
+                            [[ -n ${(M)ZSH_HIGHLIGHT_TOKENS_PRECOMMANDS:#"$arg"} && -z ${(M)ZSH_HIGHLIGHT_TOKENS_PRECOMMANDS:#"$arg_raw"} ]] && ZSH_HIGHLIGHT_TOKENS_PRECOMMANDS+=($arg_raw)
                           fi
                         }
                         ;;
diff --git a/highlighters/main/test-data/alias-comment1.zsh b/highlighters/main/test-data/alias-comment1.zsh
new file mode 100644
index 0000000..a2b56c6
--- /dev/null
+++ b/highlighters/main/test-data/alias-comment1.zsh
@@ -0,0 +1,37 @@
+# -------------------------------------------------------------------------------------------------
+# Copyright (c) 2016 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
+# -------------------------------------------------------------------------------------------------
+
+# see alias-comment2.zsh
+setopt interactivecomments
+alias x=$'# foo\npwd'
+BUFFER='x'
+
+expected_region_highlight=(
+  "1 1 alias 'interactivecomments applies to aliases'" # x becomes pwd
+)
diff --git a/highlighters/main/test-data/alias-comment2.zsh b/highlighters/main/test-data/alias-comment2.zsh
new file mode 100644
index 0000000..e9ecfca
--- /dev/null
+++ b/highlighters/main/test-data/alias-comment2.zsh
@@ -0,0 +1,37 @@
+# -------------------------------------------------------------------------------------------------
+# Copyright (c) 2016 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
+# -------------------------------------------------------------------------------------------------
+
+# see alias-comment1.zsh
+setopt NO_interactivecomments
+alias x=$'# foo\npwd'
+BUFFER='x'
+
+expected_region_highlight=(
+  "1 1 unknown-token" # x becomes #
+)
diff --git a/highlighters/main/test-data/noglob-alias.zsh b/highlighters/main/test-data/noglob-alias.zsh
index 2f96445..e6c9f3c 100644
--- a/highlighters/main/test-data/noglob-alias.zsh
+++ b/highlighters/main/test-data/noglob-alias.zsh
@@ -31,6 +31,6 @@ alias x=command
 BUFFER='x ls'
 
 expected_region_highlight=(
-  "1 1 alias" # x
+  "1 1 precommand" # x
   "3 4 command" # ls
 )
diff --git a/highlighters/main/test-data/off-by-one.zsh b/highlighters/main/test-data/off-by-one.zsh
index 550c09f..3870e20 100644
--- a/highlighters/main/test-data/off-by-one.zsh
+++ b/highlighters/main/test-data/off-by-one.zsh
@@ -27,7 +27,7 @@
 # vim: ft=zsh sw=2 ts=2 et
 # -------------------------------------------------------------------------------------------------
 
-alias a=A
+alias a=:
 f() {}
 
 BUFFER='a;f;'