diff --git a/pkg/sources/filesystem/filesystem.go b/pkg/sources/filesystem/filesystem.go
index 5f47ffa47c7f..9a1c4ceb9975 100644
--- a/pkg/sources/filesystem/filesystem.go
+++ b/pkg/sources/filesystem/filesystem.go
@@ -119,12 +119,7 @@ func (s *Source) scanDir(ctx context.Context, path string, chunksChan chan *sour
 		// Skip over non-regular files. We do this check here to suppress noisy
 		// logs for trying to scan directories and other non-regular files in
 		// our traversal.
-		fileStat, err := os.Stat(fullPath)
-		if err != nil {
-			ctx.Logger().Info("unable to stat file", "path", fullPath, "error", err)
-			return nil
-		}
-		if !fileStat.Mode().IsRegular() {
+		if !d.Type().IsRegular() {
 			return nil
 		}
 		if s.filter != nil && !s.filter.Pass(fullPath) {
@@ -223,9 +218,35 @@ func (s *Source) scanFile(ctx context.Context, path string, chunksChan chan *sou
 // filepath or a directory.
 func (s *Source) Enumerate(ctx context.Context, reporter sources.UnitReporter) error {
 	for _, path := range s.paths {
-		item := sources.CommonSourceUnit{ID: path}
-		if err := reporter.UnitOk(ctx, item); err != nil {
-			return err
+		fileInfo, err := os.Stat(filepath.Clean(path))
+		if err != nil {
+			if err := reporter.UnitErr(ctx, err); err != nil {
+				return err
+			}
+			continue
+		}
+		if !fileInfo.IsDir() {
+			item := sources.CommonSourceUnit{ID: path}
+			if err := reporter.UnitOk(ctx, item); err != nil {
+				return err
+			}
+			continue
+		}
+		err = fs.WalkDir(os.DirFS(path), ".", func(relativePath string, d fs.DirEntry, err error) error {
+			if err != nil {
+				return reporter.UnitErr(ctx, err)
+			}
+			if d.IsDir() {
+				return nil
+			}
+			fullPath := filepath.Join(path, relativePath)
+			item := sources.CommonSourceUnit{ID: fullPath}
+			return reporter.UnitOk(ctx, item)
+		})
+		if err != nil {
+			if err := reporter.UnitErr(ctx, err); err != nil {
+				return err
+			}
 		}
 	}
 	return nil
diff --git a/pkg/sources/filesystem/filesystem_test.go b/pkg/sources/filesystem/filesystem_test.go
index e6925fafe45a..0dccb3ee5393 100644
--- a/pkg/sources/filesystem/filesystem_test.go
+++ b/pkg/sources/filesystem/filesystem_test.go
@@ -2,6 +2,7 @@ package filesystem
 
 import (
 	"os"
+	"path/filepath"
 	"strings"
 	"testing"
 	"time"
@@ -115,14 +116,36 @@ func TestScanFile(t *testing.T) {
 }
 
 func TestEnumerate(t *testing.T) {
+	// TODO: refactor to allow a virtual filesystem.
 	t.Parallel()
 	ctx := context.Background()
 
 	// Setup the connection to test enumeration.
+	dir, err := os.MkdirTemp("", "trufflehog-test-enumerate")
+	assert.NoError(t, err)
+	defer os.RemoveAll(dir)
+
 	units := []string{
 		"/one", "/two", "/three",
 		"/path/to/dir/", "/path/to/another/dir/",
 	}
+	// Prefix the units with the tempdir and create files on disk.
+	for i, unit := range units {
+		fullPath := filepath.Join(dir, unit)
+		units[i] = fullPath
+		if i < 3 {
+			f, err := os.Create(fullPath)
+			assert.NoError(t, err)
+			f.Close()
+		} else {
+			assert.NoError(t, os.MkdirAll(fullPath, 0755))
+			// Create a file in the directory for enumeration to find.
+			f, err := os.CreateTemp(fullPath, "file")
+			assert.NoError(t, err)
+			units[i] = f.Name()
+			f.Close()
+		}
+	}
 	conn, err := anypb.New(&sourcespb.Filesystem{
 		Paths:       units[0:3],
 		Directories: units[3:],