diff --git a/internal/bundles/gitignore/gitignore.go b/internal/bundles/gitignore/gitignore.go
index f76b3c7f4..db7fc4d05 100644
--- a/internal/bundles/gitignore/gitignore.go
+++ b/internal/bundles/gitignore/gitignore.go
@@ -318,8 +318,14 @@ func (ign *GitIgnoreList) match(path string, info os.FileInfo) *Match {
 
 // Match returns whether any of the globs in the ignore list match the
 // specified path. Uses the same matching rules as .gitignore files.
-func (ign *GitIgnoreList) Match(path string) *Match {
-	return ign.match(path, nil)
+func (ign *GitIgnoreList) Match(path string) (*Match, error) {
+	stat, err := ign.fs.Stat(path)
+	if err != nil {
+		if !os.IsNotExist(err) {
+			return nil, err
+		}
+	}
+	return ign.match(path, stat), nil
 }
 
 // Walk walks the file tree with the specified root and calls fn on each file
diff --git a/internal/bundles/gitignore/gitignore_test.go b/internal/bundles/gitignore/gitignore_test.go
index d0b247d15..9463a0f3a 100644
--- a/internal/bundles/gitignore/gitignore_test.go
+++ b/internal/bundles/gitignore/gitignore_test.go
@@ -57,11 +57,13 @@ func (s *GitIgnoreSuite) TestMatch() {
 	s.NoError(err)
 
 	// Match returns nil if no match
-	m := ign.Match("app.py")
+	m, err := ign.Match("app.py")
+	s.NoError(err)
 	s.Nil(m)
 
 	// File matches include file info
-	m = ign.Match(".Rhistory")
+	m, err = ign.Match(".Rhistory")
+	s.NoError(err)
 	s.NotNil(m)
 	s.Equal(MatchSourceFile, m.Source)
 	s.Equal(".Rhistory", m.Pattern)
@@ -69,10 +71,25 @@ func (s *GitIgnoreSuite) TestMatch() {
 	s.Equal(1, m.Line)
 
 	// Non-file matches don't include file info
-	m = ign.Match("app.py.bak")
+	m, err = ign.Match("app.py.bak")
+	s.NoError(err)
 	s.NotNil(m)
 	s.Equal(MatchSourceUser, m.Source)
 	s.Equal("*.bak", m.Pattern)
 	s.Equal("", m.FilePath)
 	s.Equal(0, m.Line)
+
+	ignoredir := s.cwd.Join("ignoredir")
+	err = ignoredir.MkdirAll(0700)
+	s.NoError(err)
+	err = ign.AppendGlobs([]string{"ignoredir/"}, MatchSourceUser)
+	s.NoError(err)
+
+	m, err = ign.Match(ignoredir.Path())
+	s.NoError(err)
+	s.NotNil(m)
+	s.Equal(MatchSourceUser, m.Source)
+	s.Equal("ignoredir/", m.Pattern)
+	s.Equal("", m.FilePath)
+	s.Equal(0, m.Line)
 }
diff --git a/internal/bundles/gitignore/interface.go b/internal/bundles/gitignore/interface.go
index 0ab74568d..0a9721be8 100644
--- a/internal/bundles/gitignore/interface.go
+++ b/internal/bundles/gitignore/interface.go
@@ -12,7 +12,7 @@ type IgnoreList interface {
 	Append(path util.Path) error
 	AppendGlobs(patterns []string, source MatchSource) error
 	AppendGit() error
-	Match(path string) *Match
+	Match(path string) (*Match, error)
 	Walk(root util.Path, fn util.WalkFunc) error
 }
 
@@ -38,9 +38,9 @@ func (m *MockGitIgnoreList) AppendGit() error {
 	return args.Error(0)
 }
 
-func (m *MockGitIgnoreList) Match(path string) bool {
+func (m *MockGitIgnoreList) Match(path string) (*Match, error) {
 	args := m.Called(path)
-	return args.Bool(0)
+	return args.Get(0).(*Match), args.Error(1)
 }
 
 func (m *MockGitIgnoreList) Walk(root util.Path, fn util.WalkFunc) error {
@@ -48,6 +48,8 @@ func (m *MockGitIgnoreList) Walk(root util.Path, fn util.WalkFunc) error {
 	return args.Error(0)
 }
 
+var _ IgnoreList = &MockGitIgnoreList{}
+
 // Maintain a reference to the original gitignore so it
 // and its license remain in our vendor directory.
 type _ gitignore.IgnoreList
diff --git a/internal/services/api/files/files.go b/internal/services/api/files/files.go
index eee18ad19..4770d2bc9 100644
--- a/internal/services/api/files/files.go
+++ b/internal/services/api/files/files.go
@@ -86,7 +86,11 @@ func (f *File) insert(root util.Path, path util.Path, ignore gitignore.IgnoreLis
 		}
 
 		// otherwise, create it
-		exclusion := ignore.Match(path.Path())
+		exclusion, err := ignore.Match(path.Path())
+		if err != nil {
+			return nil, err
+		}
+
 		child, err := CreateFile(root, path, exclusion)
 		if err != nil {
 			return nil, err
diff --git a/internal/services/api/files/services.go b/internal/services/api/files/services.go
index 71a698900..59ef7b3b1 100644
--- a/internal/services/api/files/services.go
+++ b/internal/services/api/files/services.go
@@ -38,7 +38,11 @@ type filesService struct {
 
 func (s filesService) GetFile(p util.Path) (*File, error) {
 	p = p.Clean()
-	m := s.ignore.Match(p.String())
+	m, err := s.ignore.Match(p.String())
+	if err != nil {
+		return nil, err
+	}
+
 	file, err := CreateFile(s.root, p, m)
 	if err != nil {
 		return nil, err
diff --git a/test/sample-content/fastapi-simple/.gitignore b/test/sample-content/fastapi-simple/.gitignore
new file mode 100644
index 000000000..1d17dae13
--- /dev/null
+++ b/test/sample-content/fastapi-simple/.gitignore
@@ -0,0 +1 @@
+.venv