diff --git a/lexers/c/caddyfile.go b/lexers/c/caddyfile.go
new file mode 100644
index 000000000..e8e6e9f3a
--- /dev/null
+++ b/lexers/c/caddyfile.go
@@ -0,0 +1,205 @@
+package c
+
+import (
+	. "github.com/alecthomas/chroma" // nolint
+	"github.com/alecthomas/chroma/lexers/internal"
+)
+
+// CaddyfileCommon are the rules common to both of the lexer variants
+var CaddyfileCommon = Rules{
+	"site_block_common": {
+		// Import keyword
+		{`(import)(\s+)([^\s]+)`, ByGroups(Keyword, Text, NameVariableMagic), nil},
+		// Matcher definition
+		{`@[^\s]+\s+`, NameDecorator, Push("matcher")},
+		// These are special, they can nest more directives
+		{`handle|route|handle_path|not`, Keyword, Push("nested_directive")},
+		// Any other directive
+		{`[^\s#]+`, Keyword, Push("directive")},
+		Include("base"),
+	},
+	"matcher": {
+		{`\{`, Punctuation, Push("block")},
+		// Not can be one-liner
+		{`not`, Keyword, Push("deep_not_matcher")},
+		// Any other same-line matcher
+		{`[^\s#]+`, Keyword, Push("arguments")},
+		// Terminators
+		{`\n`, Text, Pop(1)},
+		{`\}`, Punctuation, Pop(1)},
+		Include("base"),
+	},
+	"block": {
+		{`\}`, Punctuation, Pop(2)},
+		// Not can be one-liner
+		{`not`, Keyword, Push("not_matcher")},
+		// Any other subdirective
+		{`[^\s#]+`, Keyword, Push("subdirective")},
+		Include("base"),
+	},
+	"nested_block": {
+		{`\}`, Punctuation, Pop(2)},
+		// Matcher definition
+		{`@[^\s]+\s+`, NameDecorator, Push("matcher")},
+		// Any other directive
+		{`[^\s#]+`, Keyword, Push("nested_directive")},
+		Include("base"),
+	},
+	"not_matcher": {
+		{`\}`, Punctuation, Pop(2)},
+		{`\{(?=\s)`, Punctuation, Push("block")},
+		{`[^\s#]+`, Keyword, Push("arguments")},
+		{`\s+`, Text, nil},
+	},
+	"deep_not_matcher": {
+		{`\}`, Punctuation, Pop(2)},
+		{`\{(?=\s)`, Punctuation, Push("block")},
+		{`[^\s#]+`, Keyword, Push("deep_subdirective")},
+		{`\s+`, Text, nil},
+	},
+	"directive": {
+		{`\{(?=\s)`, Punctuation, Push("block")},
+		Include("matcher_token"),
+		Include("comments_pop"),
+		{`\n`, Text, Pop(1)},
+		Include("base"),
+	},
+	"nested_directive": {
+		{`\{(?=\s)`, Punctuation, Push("nested_block")},
+		Include("matcher_token"),
+		Include("comments_pop"),
+		{`\n`, Text, Pop(1)},
+		Include("base"),
+	},
+	"subdirective": {
+		{`\{(?=\s)`, Punctuation, Push("block")},
+		Include("comments_pop"),
+		{`\n`, Text, Pop(1)},
+		Include("base"),
+	},
+	"arguments": {
+		{`\{(?=\s)`, Punctuation, Push("block")},
+		Include("comments_pop"),
+		{`\n`, Text, Pop(2)},
+		Include("base"),
+	},
+	"deep_subdirective": {
+		{`\{(?=\s)`, Punctuation, Push("block")},
+		Include("comments_pop"),
+		{`\n`, Text, Pop(3)},
+		Include("base"),
+	},
+	"matcher_token": {
+		{`@[^\s]+`, NameDecorator, Push("arguments")},         // Named matcher
+		{`/[^\s]+`, NameDecorator, Push("arguments")},         // Path matcher
+		{`\*`, NameDecorator, Push("arguments")},              // Wildcard path matcher
+		{`\[\<matcher\>\]`, NameDecorator, Push("arguments")}, // Matcher token stub for docs
+	},
+	"comments": {
+		{`^#.*\n`, CommentSingle, nil},   // Comment at start of line
+		{`\s+#.*\n`, CommentSingle, nil}, // Comment preceded by whitespace
+	},
+	"comments_pop": {
+		{`^#.*\n`, CommentSingle, Pop(1)},   // Comment at start of line
+		{`\s+#.*\n`, CommentSingle, Pop(1)}, // Comment preceded by whitespace
+	},
+	"base": {
+		Include("comments"),
+		{`on|off`, NameConstant, nil},
+		{`(https?://)?([a-z0-9.-]+)(:)([0-9]+)`, ByGroups(Name, Name, Punctuation, LiteralNumberInteger), nil},
+		{`[a-z-]+/[a-z-+]+`, LiteralString, nil},
+		{`[0-9]+[km]?\b`, LiteralNumberInteger, nil},
+		{`\{[\w+.-]+\}`, NameAttribute, nil}, // Placeholder
+		{`[^\s#{}$]+`, LiteralString, nil},
+		{`/[^\s#]*`, Name, nil},
+		{`\s+`, Text, nil},
+	},
+}
+
+// CaddyfileRules are the merged rules for the main Caddyfile lexer
+var CaddyfileRules = (func(a Rules, b Rules) Rules {
+	for k, v := range b {
+		a[k] = v
+	}
+	return a
+})(
+	Rules{
+		"root": {
+			Include("comments"),
+			// Global options block
+			{`^\s*(\{)\s*$`, ByGroups(Punctuation), Push("globals")},
+			// Snippets
+			{`(\([^\s#]+\))(\s*)(\{)`, ByGroups(NameVariableAnonymous, Text, Punctuation), Push("snippet")},
+			// Site label
+			{`[^#{(\s,]+`, NameLabel, Push("label")},
+			// Site label with placeholder
+			{`\{[\w+.-]+\}`, NameAttribute, Push("label")},
+			{`\s+`, Text, nil},
+		},
+		"globals": {
+			{`\}`, Punctuation, Pop(1)},
+			{`[^\s#]+`, KeywordType, Push("directive")},
+			Include("base"),
+		},
+		"snippet": {
+			{`\}`, Punctuation, Pop(1)},
+			// Matcher definition
+			{`@[^\s]+\s+`, NameDecorator, Push("matcher")},
+			// Any directive
+			{`[^\s#]+`, KeywordType, Push("directive")},
+			Include("base"),
+		},
+		"label": {
+			{`,`, Text, nil},
+			{` `, Text, nil},
+			{`[^#{(\s,]+`, NameLabel, nil},
+			// Comment after non-block label (hack because comments end in \n)
+			{`#.*\n`, CommentSingle, Push("site_block")},
+			// Note: if \n, we'll never pop out of the site_block, it's valid
+			{`\{(?=\s)|\n`, Punctuation, Push("site_block")},
+		},
+		"site_block": {
+			{`\}`, Punctuation, Pop(2)},
+			Include("site_block_common"),
+		},
+	},
+	CaddyfileCommon,
+)
+
+// CaddyfileDirectiveRules are the merged rules for the secondary lexer
+var CaddyfileDirectiveRules = (func(a Rules, b Rules) Rules {
+	for k, v := range b {
+		a[k] = v
+	}
+	return a
+})(
+	Rules{
+		// Same as "site_block" in Caddyfile
+		"root": {
+			Include("site_block_common"),
+		},
+	},
+	CaddyfileCommon,
+)
+
+// Caddyfile lexer.
+var Caddyfile = internal.Register(MustNewLexer(
+	&Config{
+		Name:      "Caddyfile",
+		Aliases:   []string{"caddyfile", "caddy"},
+		Filenames: []string{"Caddyfile*"},
+		MimeTypes: []string{},
+	},
+	CaddyfileRules,
+))
+
+// Caddyfile directive-only lexer.
+var CaddyfileDirectives = internal.Register(MustNewLexer(
+	&Config{
+		Name:      "Caddyfile Directives",
+		Aliases:   []string{"caddyfile-directives", "caddyfile-d", "caddy-d"},
+		Filenames: []string{},
+		MimeTypes: []string{},
+	},
+	CaddyfileDirectiveRules,
+))
diff --git a/lexers/testdata/caddyfile.actual b/lexers/testdata/caddyfile.actual
new file mode 100644
index 000000000..9f6767efb
--- /dev/null
+++ b/lexers/testdata/caddyfile.actual
@@ -0,0 +1,70 @@
+{
+	debug
+	admin off
+	on_demand_tls {
+		ask https://example.com
+	}
+}
+
+(blocking) {  
+	@blocked {
+		path *.txt *.md *.mdown /site/*
+	}
+	redir @blocked /
+}
+
+example.com, fake.org {
+	root * /srv
+
+	tls off
+
+	route {
+		# Add trailing slash for directory requests
+		@canonicalPath {
+			file {
+				try_files {path}/index.php
+			}
+			not path */
+		}
+		redir @canonicalPath {path}/ 308
+
+		# If the requested file does not exist, try index files
+		@indexFiles {
+			file {
+				try_files {path} {path}/index.php index.php
+				split_path .php
+			}
+		}
+		rewrite @indexFiles {http.matchers.file.relative}
+
+		# Proxy PHP files to the FastCGI responder
+		@phpFiles {
+			path *.php
+		}
+		reverse_proxy @phpFiles unix//var/run/php7.4-fpm.sock {
+			transport fastcgi {
+				split .php
+			}
+		}
+	}
+
+	@encode_exts {
+		path / *.html *.js *.css *.svg
+	}
+
+	header {
+		X-Content-Type-Options nosniff
+		X-XSS-Protection "1; mode=block"
+		X-Robots-Tag none
+		Content-Security-Policy "frame-ancestors 'self'"
+		X-Frame-Options DENY
+		Referrer-Policy same-origin
+	}
+
+	@singleLine not path /matcher
+	respond @singleLine "Awesome."
+
+	import blocking
+
+	file_server
+}
\ No newline at end of file
diff --git a/lexers/testdata/caddyfile.expected b/lexers/testdata/caddyfile.expected
new file mode 100644
index 000000000..989fd9481
--- /dev/null
+++ b/lexers/testdata/caddyfile.expected
@@ -0,0 +1,239 @@
+[
+  {"type":"Punctuation","value":"{"},
+  {"type":"Text","value":"\n\t"},
+  {"type":"KeywordType","value":"debug"},
+  {"type":"Text","value":"\n\t"},
+  {"type":"KeywordType","value":"admin"},
+  {"type":"Text","value":" "},
+  {"type":"NameConstant","value":"off"},
+  {"type":"Text","value":"\n\t"},
+  {"type":"KeywordType","value":"on_demand_tls"},
+  {"type":"Text","value":" "},
+  {"type":"Punctuation","value":"{"},
+  {"type":"Text","value":"\n\t\t"},
+  {"type":"Keyword","value":"ask"},
+  {"type":"Text","value":" "},
+  {"type":"LiteralString","value":"https://example.com"},
+  {"type":"Text","value":"\n\t"},
+  {"type":"Punctuation","value":"}"},
+  {"type":"Text","value":"\n"},
+  {"type":"Punctuation","value":"}"},
+  {"type":"Text","value":"\n\n"},
+  {"type":"NameVariableAnonymous","value":"(blocking)"},
+  {"type":"Text","value":" "},
+  {"type":"Punctuation","value":"{"},
+  {"type":"Text","value":"  \n\t"},
+  {"type":"NameDecorator","value":"@blocked "},
+  {"type":"Punctuation","value":"{"},
+  {"type":"Text","value":"\n\t\t"},
+  {"type":"Keyword","value":"path"},
+  {"type":"Text","value":" "},
+  {"type":"LiteralString","value":"*.txt"},
+  {"type":"Text","value":" "},
+  {"type":"LiteralString","value":"*.md"},
+  {"type":"Text","value":" "},
+  {"type":"LiteralString","value":"*.mdown"},
+  {"type":"Text","value":" "},
+  {"type":"LiteralString","value":"/site/*"},
+  {"type":"Text","value":"\n\t"},
+  {"type":"Punctuation","value":"}"},
+  {"type":"Text","value":"\n\t"},
+  {"type":"KeywordType","value":"redir"},
+  {"type":"Text","value":" "},
+  {"type":"NameDecorator","value":"@blocked"},
+  {"type":"Text","value":" "},
+  {"type":"LiteralString","value":"/"},
+  {"type":"Text","value":"\n"},
+  {"type":"Punctuation","value":"}"},
+  {"type":"Text","value":"\n\n"},
+  {"type":"NameLabel","value":"example.com"},
+  {"type":"Text","value":", "},
+  {"type":"NameLabel","value":"fake.org"},
+  {"type":"Text","value":" "},
+  {"type":"Punctuation","value":"{"},
+  {"type":"Text","value":"\n\t"},
+  {"type":"Keyword","value":"root"},
+  {"type":"Text","value":" "},
+  {"type":"NameDecorator","value":"*"},
+  {"type":"Text","value":" "},
+  {"type":"LiteralString","value":"/srv"},
+  {"type":"Text","value":"\n\n\t"},
+  {"type":"Keyword","value":"tls"},
+  {"type":"Text","value":" "},
+  {"type":"NameConstant","value":"off"},
+  {"type":"Text","value":"\n\n\t"},
+  {"type":"Keyword","value":"route"},
+  {"type":"Text","value":" "},
+  {"type":"Punctuation","value":"{"},
+  {"type":"CommentSingle","value":"\n\t\t# Add trailing slash for directory requests\n"},
+  {"type":"Text","value":"\t\t"},
+  {"type":"NameDecorator","value":"@canonicalPath "},
+  {"type":"Punctuation","value":"{"},
+  {"type":"Text","value":"\n\t\t\t"},
+  {"type":"Keyword","value":"file"},
+  {"type":"Text","value":" "},
+  {"type":"Punctuation","value":"{"},
+  {"type":"Text","value":"\n\t\t\t\t"},
+  {"type":"Keyword","value":"try_files"},
+  {"type":"Text","value":" "},
+  {"type":"NameAttribute","value":"{path}"},
+  {"type":"LiteralString","value":"/index.php"},
+  {"type":"Text","value":"\n\t\t\t"},
+  {"type":"Punctuation","value":"}"},
+  {"type":"Text","value":"\n\t\t\t"},
+  {"type":"Keyword","value":"not"},
+  {"type":"Text","value":" "},
+  {"type":"Keyword","value":"path"},
+  {"type":"Text","value":" "},
+  {"type":"LiteralString","value":"*/"},
+  {"type":"Text","value":"\n\t\t"},
+  {"type":"Punctuation","value":"}"},
+  {"type":"Text","value":"\n\t\t"},
+  {"type":"Keyword","value":"redir"},
+  {"type":"Text","value":" "},
+  {"type":"NameDecorator","value":"@canonicalPath"},
+  {"type":"Text","value":" "},
+  {"type":"NameAttribute","value":"{path}"},
+  {"type":"LiteralString","value":"/"},
+  {"type":"Text","value":" "},
+  {"type":"LiteralNumberInteger","value":"308"},
+  {"type":"CommentSingle","value":"\n\n\t\t# If the requested file does not exist, try index files\n"},
+  {"type":"Text","value":"\t\t"},
+  {"type":"NameDecorator","value":"@indexFiles"},
+  {"type":"Text","value":" "},
+  {"type":"Punctuation","value":"{"},
+  {"type":"Text","value":"\n\t\t\t"},
+  {"type":"Keyword","value":"file"},
+  {"type":"Text","value":" "},
+  {"type":"Punctuation","value":"{"},
+  {"type":"Text","value":"\n\t\t\t\t"},
+  {"type":"Keyword","value":"try_files"},
+  {"type":"Text","value":" "},
+  {"type":"NameAttribute","value":"{path}"},
+  {"type":"Text","value":" "},
+  {"type":"NameAttribute","value":"{path}"},
+  {"type":"LiteralString","value":"/index.php"},
+  {"type":"Text","value":" "},
+  {"type":"LiteralString","value":"index.php"},
+  {"type":"Text","value":"\n\t\t\t\t"},
+  {"type":"Keyword","value":"split_path"},
+  {"type":"Text","value":" "},
+  {"type":"LiteralString","value":".php"},
+  {"type":"Text","value":"\n\t\t\t"},
+  {"type":"Punctuation","value":"}"},
+  {"type":"Text","value":"\n\t\t"},
+  {"type":"Punctuation","value":"}"},
+  {"type":"Text","value":"\n\t\t"},
+  {"type":"Keyword","value":"rewrite"},
+  {"type":"Text","value":" "},
+  {"type":"NameDecorator","value":"@indexFiles"},
+  {"type":"Text","value":" "},
+  {"type":"NameAttribute","value":"{http.matchers.file.relative}"},
+  {"type":"CommentSingle","value":"\n\n\t\t# Proxy PHP files to the FastCGI responder\n"},
+  {"type":"Text","value":"\t\t"},
+  {"type":"NameDecorator","value":"@phpFiles"},
+  {"type":"Text","value":" "},
+  {"type":"Punctuation","value":"{"},
+  {"type":"Text","value":"\n\t\t\t"},
+  {"type":"Keyword","value":"path"},
+  {"type":"Text","value":" "},
+  {"type":"LiteralString","value":"*.php"},
+  {"type":"Text","value":"\n\t\t"},
+  {"type":"Punctuation","value":"}"},
+  {"type":"Text","value":"\n\t\t"},
+  {"type":"Keyword","value":"reverse_proxy"},
+  {"type":"Text","value":" "},
+  {"type":"NameDecorator","value":"@phpFiles"},
+  {"type":"Text","value":" "},
+  {"type":"LiteralString","value":"unix//var/run/php7.4-fpm.sock"},
+  {"type":"Text","value":" "},
+  {"type":"Punctuation","value":"{"},
+  {"type":"Text","value":"\n\t\t\t"},
+  {"type":"Keyword","value":"transport"},
+  {"type":"Text","value":" "},
+  {"type":"LiteralString","value":"fastcgi"},
+  {"type":"Text","value":" "},
+  {"type":"Punctuation","value":"{"},
+  {"type":"Text","value":"\n\t\t\t\t"},
+  {"type":"Keyword","value":"split"},
+  {"type":"Text","value":" "},
+  {"type":"LiteralString","value":".php"},
+  {"type":"Text","value":"\n\t\t\t"},
+  {"type":"Punctuation","value":"}"},
+  {"type":"Text","value":"\n\t\t"},
+  {"type":"Punctuation","value":"}"},
+  {"type":"Text","value":"\n\t"},
+  {"type":"Punctuation","value":"}"},
+  {"type":"Text","value":"\n\n\t"},
+  {"type":"NameDecorator","value":"@encode_exts "},
+  {"type":"Punctuation","value":"{"},
+  {"type":"Text","value":"\n\t\t"},
+  {"type":"Keyword","value":"path"},
+  {"type":"Text","value":" "},
+  {"type":"LiteralString","value":"/"},
+  {"type":"Text","value":" "},
+  {"type":"LiteralString","value":"*.html"},
+  {"type":"Text","value":" "},
+  {"type":"LiteralString","value":"*.js"},
+  {"type":"Text","value":" "},
+  {"type":"LiteralString","value":"*.css"},
+  {"type":"Text","value":" "},
+  {"type":"LiteralString","value":"*.svg"},
+  {"type":"Text","value":"\n\t"},
+  {"type":"Punctuation","value":"}"},
+  {"type":"Text","value":"\n\n\t"},
+  {"type":"Keyword","value":"header"},
+  {"type":"Text","value":" "},
+  {"type":"Punctuation","value":"{"},
+  {"type":"Text","value":"\n\t\t"},
+  {"type":"Keyword","value":"X-Content-Type-Options"},
+  {"type":"Text","value":" "},
+  {"type":"LiteralString","value":"nosniff"},
+  {"type":"Text","value":"\n\t\t"},
+  {"type":"Keyword","value":"X-XSS-Protection"},
+  {"type":"Text","value":" "},
+  {"type":"LiteralString","value":"\"1;"},
+  {"type":"Text","value":" "},
+  {"type":"LiteralString","value":"mode=block\""},
+  {"type":"Text","value":"\n\t\t"},
+  {"type":"Keyword","value":"X-Robots-Tag"},
+  {"type":"Text","value":" "},
+  {"type":"LiteralString","value":"none"},
+  {"type":"Text","value":"\n\t\t"},
+  {"type":"Keyword","value":"Content-Security-Policy"},
+  {"type":"Text","value":" "},
+  {"type":"LiteralString","value":"\"frame-ancestors"},
+  {"type":"Text","value":" "},
+  {"type":"LiteralString","value":"'self'\""},
+  {"type":"Text","value":"\n\t\t"},
+  {"type":"Keyword","value":"X-Frame-Options"},
+  {"type":"Text","value":" "},
+  {"type":"LiteralString","value":"DENY"},
+  {"type":"Text","value":"\n\t\t"},
+  {"type":"Keyword","value":"Referrer-Policy"},
+  {"type":"Text","value":" "},
+  {"type":"LiteralString","value":"same-origin"},
+  {"type":"Text","value":"\n\t"},
+  {"type":"Punctuation","value":"}"},
+  {"type":"Text","value":"\n\n\t"},
+  {"type":"NameDecorator","value":"@singleLine "},
+  {"type":"Keyword","value":"not"},
+  {"type":"Text","value":" "},
+  {"type":"Keyword","value":"path"},
+  {"type":"Text","value":" "},
+  {"type":"LiteralString","value":"/matcher"},
+  {"type":"Text","value":"\n\t"},
+  {"type":"Keyword","value":"respond"},
+  {"type":"Text","value":" "},
+  {"type":"NameDecorator","value":"@singleLine"},
+  {"type":"Text","value":" "},
+  {"type":"LiteralString","value":"\"Awesome.\""},
+  {"type":"Text","value":"\n\n\t"},
+  {"type":"Keyword","value":"import"},
+  {"type":"Text","value":" "},
+  {"type":"NameVariableMagic","value":"blocking"},
+  {"type":"Text","value":"\n\n\t"},
+  {"type":"Keyword","value":"file_server"},
+  {"type":"Text","value":"\n"},
+  {"type":"Punctuation","value":"}"}
+]