From 6d767a92a5e87302224b4764c3fc92dc32b6dbdc Mon Sep 17 00:00:00 2001
From: Rabeya Noor <rabeyanoor.dev@gmail.com>
Date: Mon, 21 Sep 2026 23:34:16 +0600
Subject: [PATCH] parser: treat unmatched wildcard FROM paths as missing on
 Windows

Fixes #18568
---
 parser/parser.go      | 12 ++++++++++++
 parser/parser_test.go | 17 +++++++++++++++++
 2 files changed, 29 insertions(+)

diff --git a/parser/parser.go b/parser/parser.go
index 5ca018f56..9557eb6e6 100644
--- a/parser/parser.go
+++ b/parser/parser.go
@@ -248,11 +248,23 @@ func canonicalLocalPath(path string) (string, error) {
 	return filepath.EvalSymlinks(abs)
 }
 
+// hasWildcard reports whether path has a glob wildcard outside its volume
+// name, which may legitimately contain "?" (e.g. \\?\C:\).
+func hasWildcard(path string) bool {
+	return strings.ContainsAny(path[len(filepath.VolumeName(path)):], "*?")
+}
+
 func fileDigestMap(path string) (map[string]string, error) {
 	fl := make(map[string]string)
 
 	fi, err := os.Stat(path)
 	if err != nil {
+		// Windows rejects wildcard characters in os.Stat with an invalid
+		// name error rather than ErrNotExist. A pattern that reaches here
+		// matched nothing, so report it as missing like other platforms do.
+		if runtime.GOOS == "windows" && hasWildcard(path) {
+			return nil, fmt.Errorf("%w: %s", os.ErrNotExist, path)
+		}
 		return nil, err
 	}
 
diff --git a/parser/parser_test.go b/parser/parser_test.go
index 0257c03c3..048431445 100644
--- a/parser/parser_test.go
+++ b/parser/parser_test.go
@@ -1005,6 +1005,23 @@ func TestCreateRequestFileGlobNoMatchUsesModelName(t *testing.T) {
 	}
 }
 
+func TestHasWildcard(t *testing.T) {
+	for _, tt := range []struct {
+		path string
+		want bool
+	}{
+		{"model.gguf", false},
+		{"model-*.gguf", true},
+		{"model-?.gguf", true},
+		{filepath.Join("dir", "*.gguf"), true},
+		{filepath.Join("dir", "model.gguf"), false},
+	} {
+		if got := hasWildcard(tt.path); got != tt.want {
+			t.Errorf("hasWildcard(%q) = %v, want %v", tt.path, got, tt.want)
+		}
+	}
+}
+
 func TestCreateRequestFileGlobRejectsBadPattern(t *testing.T) {
 	modelfile, err := ParseFile(strings.NewReader("FROM [\n"))
 	if err != nil {