diff --git a/src/path/filepath/path.go b/src/path/filepath/path.go
index 9772de4342..41fa733af9 100644
--- a/src/path/filepath/path.go
+++ b/src/path/filepath/path.go
@@ -16,6 +16,7 @@ import (
 	"io/fs"
 	"os"
 	"runtime"
+	"slices"
 	"sort"
 	"strings"
 )
@@ -52,6 +53,11 @@ func (b *lazybuf) append(c byte) {
 	b.w++
 }
 
+func (b *lazybuf) prepend(prefix ...byte) {
+	b.buf = slices.Insert(b.buf, 0, prefix...)
+	b.w += len(prefix)
+}
+
 func (b *lazybuf) string() string {
 	if b.buf == nil {
 		return b.volAndPath[:b.volLen+b.w]
@@ -150,18 +156,6 @@ func Clean(path string) string {
 			if rooted && out.w != 1 || !rooted && out.w != 0 {
 				out.append(Separator)
 			}
-			// If a ':' appears in the path element at the start of a Windows path,
-			// insert a .\ at the beginning to avoid converting relative paths
-			// like a/../c: into c:.
-			if runtime.GOOS == "windows" && out.w == 0 && out.volLen == 0 && r != 0 {
-				for i := r; i < n && !os.IsPathSeparator(path[i]); i++ {
-					if path[i] == ':' {
-						out.append('.')
-						out.append(Separator)
-						break
-					}
-				}
-			}
 			// copy element
 			for ; r < n && !os.IsPathSeparator(path[r]); r++ {
 				out.append(path[r])
@@ -174,6 +168,21 @@ func Clean(path string) string {
 		out.append('.')
 	}
 
+	if runtime.GOOS == "windows" && out.volLen == 0 && out.buf != nil {
+		// If a ':' appears in the path element at the start of a Windows path,
+		// insert a .\ at the beginning to avoid converting relative paths
+		// like a/../c: into c:.
+		for _, c := range out.buf {
+			if os.IsPathSeparator(c) {
+				break
+			}
+			if c == ':' {
+				out.prepend('.', Separator)
+				break
+			}
+		}
+	}
+
 	return FromSlash(out.string())
 }
 
diff --git a/src/path/filepath/path_test.go b/src/path/filepath/path_test.go
index 3c78e415d2..621208d31e 100644
--- a/src/path/filepath/path_test.go
+++ b/src/path/filepath/path_test.go
@@ -67,6 +67,7 @@ var cleantests = []PathTest{
 	{"/abc/def/../../..", "/"},
 	{"abc/def/../../../ghi/jkl/../../../mno", "../../mno"},
 	{"/../abc", "/abc"},
+	{"a/../b:/../../c", `../c`},
 
 	// Combinations
 	{"abc/./../def", "def"},
@@ -89,6 +90,7 @@ var wincleantests = []PathTest{
 	{`c:\abc\def\..\..`, `c:\`},
 	{`c:\..\abc`, `c:\abc`},
 	{`c:..\abc`, `c:..\abc`},
+	{`c:\b:\..\..\..\d`, `c:\d`},
 	{`\`, `\`},
 	{`/`, `\`},
 	{`\\i\..\c$`, `\\i\..\c$`},
@@ -169,6 +171,7 @@ var islocaltests = []IsLocalTest{
 	{"a/", true},
 	{"a/.", true},
 	{"a/./b/./c", true},
+	{`a/../b:/../../c`, false},
 }
 
 var winislocaltests = []IsLocalTest{
@@ -380,6 +383,7 @@ var winjointests = []JoinTest{
 	{[]string{`\\a`, `b`, `c`}, `\\a\b\c`},
 	{[]string{`\\a\`, `b`, `c`}, `\\a\b\c`},
 	{[]string{`//`, `a`}, `\\a`},
+	{[]string{`a:\b\c`, `x\..\y:\..\..\z`}, `a:\b\z`},
 }
 
 func TestJoin(t *testing.T) {