diff --git a/components/prism-shell-session.js b/components/prism-shell-session.js
index 652de04624..1b67ed76cf 100644
--- a/components/prism-shell-session.js
+++ b/components/prism-shell-session.js
@@ -33,7 +33,7 @@
 				// shell symbol
 				/[$#%](?=\s)/.source +
 				// bash command
-				/(?:[^\\\r\n'"<$]|\\(?:[^\r]|\r\n?)|\$(?!')|<<str>>)+/.source.replace(/<<str>>/g, function () { return strings; }),
+				/(?:[^\\\r\n \t'"<$]|[ \t](?:(?!#)|#.*$)|\\(?:[^\r]|\r\n?)|\$(?!')|<(?!<)|<<str>>)+/.source.replace(/<<str>>/g, function () { return strings; }),
 				'm'
 			),
 			greedy: true,
diff --git a/components/prism-shell-session.min.js b/components/prism-shell-session.min.js
index e9c36cf35f..74810323c7 100644
--- a/components/prism-shell-session.min.js
+++ b/components/prism-shell-session.min.js
@@ -1 +1 @@
-!function(s){var n=['"(?:\\\\[^]|\\$\\([^)]+\\)|\\$(?!\\()|`[^`]+`|[^"\\\\`$])*"',"'[^']*'","\\$'(?:[^'\\\\]|\\\\[^])*'","<<-?\\s*([\"']?)(\\w+)\\1\\s[^]*?[\r\n]\\2"].join("|");s.languages["shell-session"]={command:{pattern:RegExp('^(?:[^\\s@:$#%*!/\\\\]+@[^\r\n@:$#%*!/\\\\]+(?::[^\0-\\x1F$#%*?"<>:;|]+)?|[/~.][^\0-\\x1F$#%*?"<>@:;|]*)?[$#%](?=\\s)'+"(?:[^\\\\\r\n'\"<$]|\\\\(?:[^\r]|\r\n?)|\\$(?!')|<<str>>)+".replace(/<<str>>/g,function(){return n}),"m"),greedy:!0,inside:{info:{pattern:/^[^#$%]+/,alias:"punctuation",inside:{user:/^[^\s@:$#%*!/\\]+@[^\r\n@:$#%*!/\\]+/,punctuation:/:/,path:/[\s\S]+/}},bash:{pattern:/(^[$#%]\s*)\S[\s\S]*/,lookbehind:!0,alias:"language-bash",inside:s.languages.bash},"shell-symbol":{pattern:/^[$#%]/,alias:"important"}}},output:/.(?:.*(?:[\r\n]|.$))*/},s.languages["sh-session"]=s.languages.shellsession=s.languages["shell-session"]}(Prism);
\ No newline at end of file
+!function(s){var n=['"(?:\\\\[^]|\\$\\([^)]+\\)|\\$(?!\\()|`[^`]+`|[^"\\\\`$])*"',"'[^']*'","\\$'(?:[^'\\\\]|\\\\[^])*'","<<-?\\s*([\"']?)(\\w+)\\1\\s[^]*?[\r\n]\\2"].join("|");s.languages["shell-session"]={command:{pattern:RegExp('^(?:[^\\s@:$#%*!/\\\\]+@[^\r\n@:$#%*!/\\\\]+(?::[^\0-\\x1F$#%*?"<>:;|]+)?|[/~.][^\0-\\x1F$#%*?"<>@:;|]*)?[$#%](?=\\s)'+"(?:[^\\\\\r\n \t'\"<$]|[ \t](?:(?!#)|#.*$)|\\\\(?:[^\r]|\r\n?)|\\$(?!')|<(?!<)|<<str>>)+".replace(/<<str>>/g,function(){return n}),"m"),greedy:!0,inside:{info:{pattern:/^[^#$%]+/,alias:"punctuation",inside:{user:/^[^\s@:$#%*!/\\]+@[^\r\n@:$#%*!/\\]+/,punctuation:/:/,path:/[\s\S]+/}},bash:{pattern:/(^[$#%]\s*)\S[\s\S]*/,lookbehind:!0,alias:"language-bash",inside:s.languages.bash},"shell-symbol":{pattern:/^[$#%]/,alias:"important"}}},output:/.(?:.*(?:[\r\n]|.$))*/},s.languages["sh-session"]=s.languages.shellsession=s.languages["shell-session"]}(Prism);
\ No newline at end of file
diff --git a/tests/languages/shell-session/command_string_feature.test b/tests/languages/shell-session/command_string_feature.test
index 854314b8bb..930d0b62ca 100644
--- a/tests/languages/shell-session/command_string_feature.test
+++ b/tests/languages/shell-session/command_string_feature.test
@@ -21,6 +21,9 @@ $ cat << "EOF" > /etc/ipsec.secrets
 # : RSA vpn-server-b.key
 EOF
 
+$ LC_ALL=C tr -cd 'a-zA-Z0-9_-;:!?.@\\*/#%$' < /dev/random | head -c 8
+y_#!$U48
+
 ----------------------------------------------------
 
 [
@@ -64,10 +67,10 @@ EOF
 			["builtin", "echo"],
 			["punctuation", "\\"],
 			"'a ",
-			["comment", "# "]
+			["comment", "# '"]
 		]]
 	]],
-	["output", "'\r\n\r\n"],
+
 	["command", [
 		["shell-symbol", "$"],
 		["bash", [
@@ -83,7 +86,28 @@ EOF
 				"\r\n: RSA vpn-server-a.key\r\n# : RSA vpn-server-b.key\r\nEOF"
 			]]
 		]]
-	]]
+	]],
+
+	["command", [
+		["shell-symbol", "$"],
+		["bash", [
+			["assign-left", [
+				["environment", "LC_ALL"]
+			]],
+			["operator", ["="]],
+			"C ",
+			["function", "tr"],
+			" -cd ",
+			["string", "'a-zA-Z0-9_-;:!?.@\\\\*/#%$'"],
+			["operator", ["<"]],
+			" /dev/random ",
+			["operator", ["|"]],
+			["function", "head"],
+			" -c ",
+			["number", "8"]
+		]]
+	]],
+	["output", "y_#!$U48"]
 ]
 
 ----------------------------------------------------