diff --git a/commands/cli/parse.go b/commands/cli/parse.go
index c6faf374ce5c..99a90309c4f3 100644
--- a/commands/cli/parse.go
+++ b/commands/cli/parse.go
@@ -399,8 +399,18 @@ func getArgDef(i int, argDefs []cmds.Argument) *cmds.Argument {
 
 const notRecursiveFmtStr = "'%s' is a directory, use the '-%s' flag to specify directories"
 const dirNotSupportedFmtStr = "Invalid path '%s', argument '%s' does not support directories"
+const winDriveLetterFmtStr = "%q is a drive letter not a drive path, append a \\ to your input"
 
 func appendFile(fpath string, argDef *cmds.Argument, recursive, hidden bool) (files.File, error) {
+	// resolve Windows relative dot paths like X:.\somepath
+	if len(fpath) >= 3 && fpath[0] != '/' && fpath[1:3] == ":." {
+		var err error
+		fpath, err = filepath.Abs(fpath)
+		if err != nil {
+			return nil, err
+		}
+	}
+
 	if fpath == "." {
 		cwd, err := os.Getwd()
 		if err != nil {
@@ -429,10 +439,29 @@ func appendFile(fpath string, argDef *cmds.Argument, recursive, hidden bool) (fi
 		}
 	}
 
-	// special case for Windows drive roots i.e. X:\
-	// drive path must be preserved and not converted to X: or /
-	if len(fpath) == 3 && fpath[0] != '/' && fpath[1:3] == `:\` {
-		return files.NewSerialFile(fpath, fpath, hidden, stat)
+	// special cases for Windows drive roots i.e. X:\ and their long form \\?\X:\
+	// drive path must be preserved and not converted to `X:`, `X:.`, or `/`
+	switch len(fpath) {
+	case 3:
+		// X: will be cleaned to `X:.` which is not what is intended, a case for handling dot relative paths is above
+		if fpath[0] != '/' && fpath[1:3] == ":." {
+			return nil, fmt.Errorf(winDriveLetterFmtStr, fpath[:2])
+		}
+		// X:\ needs to preserve the `\`, path.Base would remove it
+		if fpath[0] != '/' && fpath[1:3] == ":\\" {
+			return files.NewSerialFile(fpath, fpath, hidden, stat)
+		}
+	case 6:
+		// \\?\X: long prefix form of X:
+		if fpath[:4] == "\\\\?\\" && fpath[5] == ':' {
+			return nil, fmt.Errorf(winDriveLetterFmtStr, fpath)
+		}
+	case 7:
+		// \\?\X:\ long prefix form of X:\
+		if fpath[:4] == "\\\\?\\" && fpath[5] == ':' && fpath[6] == '\\' {
+			fpath = string(fpath[4]) + ":\\"
+			return files.NewSerialFile(fpath, fpath, hidden, stat)
+		}
 	}
 
 	return files.NewSerialFile(path.Base(filepath.ToSlash(fpath)), fpath, hidden, stat)