diff --git a/internal/buffer/buffer.go b/internal/buffer/buffer.go
index d1f8db4b2b..08666e304b 100644
--- a/internal/buffer/buffer.go
+++ b/internal/buffer/buffer.go
@@ -866,7 +866,7 @@ func (b *Buffer) UpdateRules() {
 		matchedFileHeader := false
 
 		if ft == "unknown" || ft == "" {
-			if header.MatchFileName(b.Path) {
+			if header.MatchFilePath(b.AbsPath) {
 				matchedFileName = true
 			}
 			if len(fnameMatches) == 0 && header.MatchFileHeader(b.lines[0].data) {
@@ -920,7 +920,7 @@ func (b *Buffer) UpdateRules() {
 			}
 
 			if ft == "unknown" || ft == "" {
-				if header.MatchFileName(b.Path) {
+				if header.MatchFilePath(b.AbsPath) {
 					fnameMatches = append(fnameMatches, syntaxFileInfo{header, f.Name(), nil})
 				}
 				if len(fnameMatches) == 0 && header.MatchFileHeader(b.lines[0].data) {
diff --git a/pkg/highlight/parser.go b/pkg/highlight/parser.go
index 804e6bc0bd..7d7e1480b3 100644
--- a/pkg/highlight/parser.go
+++ b/pkg/highlight/parser.go
@@ -4,9 +4,9 @@ import (
 	"bytes"
 	"errors"
 	"fmt"
-	"regexp"
-
 	"gopkg.in/yaml.v2"
+	"path/filepath"
+	"regexp"
 )
 
 // A Group represents a syntax group
@@ -154,13 +154,25 @@ func MakeHeaderYaml(data []byte) (*Header, error) {
 	return header, nil
 }
 
-// MatchFileName will check the given file name with the stored regex
-func (header *Header) MatchFileName(filename string) bool {
-	if header.FileNameRegex != nil {
-		return header.FileNameRegex.MatchString(filename)
+// MatchFilePath will check the given file's absolute path with the stored regex;
+// Only matches which include at least part of the filename are considered.
+func (header *Header) MatchFilePath(absoluteFilePath string) bool {
+	if header.FileNameRegex == nil {
+		return false
 	}
 
-	return false
+	matchBounds := header.FileNameRegex.FindAllStringIndex(absoluteFilePath, -1)
+	if matchBounds == nil {
+		return false
+	}
+
+	baseName := filepath.Base(absoluteFilePath)
+	lastMatchEnd := matchBounds[len(matchBounds)-1][1]
+
+	// If a match occurs on the absolute path, make sure the match includes part of the
+	// filename (i.e. the match extends beyond the length of the file's dir path) to
+	// avoid having just the dir path of the file trigger a match.
+	return lastMatchEnd > (len(absoluteFilePath) - len(baseName))
 }
 
 func (header *Header) MatchFileHeader(firstLine []byte) bool {
diff --git a/runtime/syntax/apacheconf.yaml b/runtime/syntax/apacheconf.yaml
index a6f89140df..27bf921a12 100644
--- a/runtime/syntax/apacheconf.yaml
+++ b/runtime/syntax/apacheconf.yaml
@@ -1,7 +1,7 @@
 filetype: apacheconf
 
 detect:
-    filename: "httpd\\.conf|mime\\.types|vhosts\\.d\\\\*|\\.htaccess"
+    filename: "httpd\\.conf|mime\\.types|vhosts\\.d(/|\\\\).*|\\.htaccess"
 
 rules:
     - identifier: "(AcceptMutex|AcceptPathInfo|AccessFileName|Action|AddAlt|AddAltByEncoding|AddAltByType|AddCharset|AddDefaultCharset|AddDescription|AddEncoding)"
diff --git a/runtime/syntax/groff.yaml b/runtime/syntax/groff.yaml
index 3eaea1f940..b6df048b6f 100644
--- a/runtime/syntax/groff.yaml
+++ b/runtime/syntax/groff.yaml
@@ -1,7 +1,7 @@
 filetype: groff
 
 detect:
-    filename: "\\.m[ems]$|\\.rof|\\.tmac$|^tmac."
+    filename: "\\.m[ems]$|\\.rof|\\.tmac$|(^|/|\\\\)tmac."
 
 rules:
     - statement: "^\\.(ds|nr) [^[[:space:]]]*"
diff --git a/runtime/syntax/groovy.yaml b/runtime/syntax/groovy.yaml
index 1830f8b5e3..a5b56a1fa3 100644
--- a/runtime/syntax/groovy.yaml
+++ b/runtime/syntax/groovy.yaml
@@ -1,7 +1,7 @@
 filetype: groovy
 
 detect:
-    filename: "(\\.(groovy|gy|gvy|gsh|gradle)$|^[Jj]enkinsfile$)"
+    filename: "(\\.(groovy|gy|gvy|gsh|gradle)$|(^|/|\\\\)[Jj]enkinsfile$)"
     header: "^#!.*/(env +)?groovy *$"
 
 rules:
diff --git a/runtime/syntax/ini.yaml b/runtime/syntax/ini.yaml
index 902d66a3b7..51222bf9fe 100644
--- a/runtime/syntax/ini.yaml
+++ b/runtime/syntax/ini.yaml
@@ -1,7 +1,7 @@
 filetype: ini
 
 detect:
-    filename: "\\.(ini|desktop|lfl|override|tscn|tres)$|(mimeapps\\.list|pinforc|setup\\.cfg|project\\.godot)$|weechat/.+\\.conf$"
+    filename: "\\.(ini|desktop|lfl|override|tscn|tres)$|(mimeapps\\.list|pinforc|setup\\.cfg|project\\.godot)$|weechat(/|\\\\).+\\.conf$"
 
 rules:
     - constant.bool.true: "\\btrue\\b"
diff --git a/runtime/syntax/justfile.yaml b/runtime/syntax/justfile.yaml
index 926edb21e2..42c4564e0e 100644
--- a/runtime/syntax/justfile.yaml
+++ b/runtime/syntax/justfile.yaml
@@ -2,7 +2,7 @@
 filetype: 'justfile'
 
 detect:
-    filename: "(^\\.?[Jj]ustfile|\\.just)$"
+    filename: "((^|/|\\\\)\\.?[Jj]ustfile|\\.just)$"
     header: "^#!.*/(env +)?[bg]?just --justfile"
 
 rules:
diff --git a/runtime/syntax/ledger.yaml b/runtime/syntax/ledger.yaml
index 0121ae0a1e..29a966bac7 100644
--- a/runtime/syntax/ledger.yaml
+++ b/runtime/syntax/ledger.yaml
@@ -1,7 +1,7 @@
 filetype: ledger
 
 detect:
-    filename: "(^|\\.|/)(ledger|ldgr|beancount|bnct)$"
+    filename: "(^|/|\\\\)\\.?(ledger|ldgr|beancount|bnct)$"
 
 rules:
     - special: "^([0-9]{4}(/|-)[0-9]{2}(/|-)[0-9]{2}|[=~]) .*"
diff --git a/runtime/syntax/mail.yaml b/runtime/syntax/mail.yaml
index 6ffe8733fd..86894026eb 100644
--- a/runtime/syntax/mail.yaml
+++ b/runtime/syntax/mail.yaml
@@ -1,7 +1,7 @@
 filetype: mail
 
 detect:
-    filename: "(.*/mutt-.*|\\.eml)$"
+    filename: "(.*(/|\\\\)mutt-.*|\\.eml)$"
     header: "^From .* \\d+:\\d+:\\d+ \\d+"
 
 rules:
diff --git a/runtime/syntax/nftables.yaml b/runtime/syntax/nftables.yaml
index 489fdb0b29..56e2c56b02 100644
--- a/runtime/syntax/nftables.yaml
+++ b/runtime/syntax/nftables.yaml
@@ -1,7 +1,7 @@
 filetype: nftables
 
 detect:
-    filename: "(nftables\\.(conf|rules)$|nftables(\\.rules)?\\.d/)"
+    filename: "(nftables\\.(conf|rules)$|nftables(\\.rules)?\\.d(/|\\\\).+)"
     header: "^(#!.*/(env +)?nft( |$)|flush +ruleset)"
 
 rules:
diff --git a/runtime/syntax/privoxy-config.yaml b/runtime/syntax/privoxy-config.yaml
index 7eb0898950..ac6fd67df9 100644
--- a/runtime/syntax/privoxy-config.yaml
+++ b/runtime/syntax/privoxy-config.yaml
@@ -1,7 +1,7 @@
 filetype: privoxy-config
 
 detect:
-    filename: "privoxy/config$"
+    filename: "privoxy(/|\\\\)config$"
 
 rules:
     - statement: "(accept-intercepted-requests|actionsfile|admin-address|allow-cgi-request-crunching|buffer-limit|compression-level|confdir|connection-sharing|debug|default-server-timeout|deny-access|enable-compression|enable-edit-actions|enable-remote-http-toggle|enable-remote-toggle|enforce-blocks|filterfile|forward|forwarded-connect-retries|forward-socks4|forward-socks4a|forward-socks5|handle-as-empty-doc-returns-ok|hostname|keep-alive-timeout|listen-address|logdir|logfile|max-client-connections|permit-access|proxy-info-url|single-threaded|socket-timeout|split-large-forms|templdir|toggle|tolerate-pipelining|trustfile|trust-info-url|user-manual)[[:space:]]"
diff --git a/runtime/syntax/vi.yaml b/runtime/syntax/vi.yaml
index 2a828dcd6d..f83c69f195 100644
--- a/runtime/syntax/vi.yaml
+++ b/runtime/syntax/vi.yaml
@@ -1,7 +1,7 @@
 filetype: vi
 
 detect:
-    filename: "(^|/|\\.)(ex|vim)rc$|\\.vim"
+    filename: "(^|/|\\\\)\\.?(ex|vim)rc$|\\.vim"
 
 rules:
     - identifier: "[A-Za-z_][A-Za-z0-9_]*[(]+[A-Za-z0-9_:.,\\s]*[)]+"