diff --git a/test/integration/path_type_change_test.go b/test/integration/path_type_change_test.go
new file mode 100644
index 00000000..998acefb
--- /dev/null
+++ b/test/integration/path_type_change_test.go
@@ -0,0 +1,62 @@
+package integration
+
+import (
+	"testing"
+
+	"github.com/anchore/stereoscope/pkg/file"
+	"github.com/anchore/stereoscope/pkg/filetree/filenode"
+	"github.com/anchore/stereoscope/pkg/imagetest"
+)
+
+func TestPathTypeChangeImage(t *testing.T) {
+	image := imagetest.GetFixtureImage(t, "docker-archive", "image-path-type-change")
+
+	layerAssertions := []map[string]file.Type{
+		make(map[string]file.Type),
+		{
+			"/chimera/a.txt": file.TypeRegular,
+			"/chimera/b.txt": file.TypeRegular,
+			"/chimera":       file.TypeDirectory,
+		},
+		{
+			"/chimera": file.TypeDirectory,
+		},
+		make(map[string]file.Type),
+		{
+			"/chimera": file.TypeRegular,
+		},
+		make(map[string]file.Type),
+		{
+			"/chimera": file.TypeSymLink,
+		},
+		make(map[string]file.Type),
+		{
+			"/chimera": file.TypeDirectory,
+		},
+	}
+
+	for idx, layer := range image.Layers {
+		assertions := layerAssertions[idx]
+		err := layer.SquashedTree.Walk(func(path file.Path, f filenode.FileNode) error {
+			expect, ok := assertions[string(path)]
+			if !ok {
+				return nil
+			}
+			if f.FileType != expect {
+				t.Errorf("at %v got %v want %v", path, f.FileType, expect)
+			}
+			delete(assertions, string(path))
+			return nil
+		}, nil)
+		if err != nil {
+			t.Error(err)
+		}
+	}
+	for i, a := range layerAssertions {
+		if len(a) > 0 {
+			for k, v := range a {
+				t.Errorf("for layer %v, never saw %v of type %v", i, k, v)
+			}
+		}
+	}
+}
diff --git a/test/integration/test-fixtures/image-path-type-change/Dockerfile b/test/integration/test-fixtures/image-path-type-change/Dockerfile
new file mode 100644
index 00000000..16a58798
--- /dev/null
+++ b/test/integration/test-fixtures/image-path-type-change/Dockerfile
@@ -0,0 +1,20 @@
+FROM busybox:1.37.0@sha256:db142d433cdde11f10ae479dbf92f3b13d693fd1c91053da9979728cceb1dc68
+
+# makes /chimera/a.txt /chimera/b.txt
+COPY . /
+
+# make a layer where the dir is empty
+RUN rm /chimera/a.txt /chimera/b.txt
+
+RUN rmdir /chimera
+
+RUN touch /chimera
+
+RUN rm /chimera
+
+RUN ln -s /etc/hostname /chimera
+
+RUN unlink /chimera
+
+RUN mkdir /chimera
+
diff --git a/test/integration/test-fixtures/image-path-type-change/chimera/a.txt b/test/integration/test-fixtures/image-path-type-change/chimera/a.txt
new file mode 100644
index 00000000..e69de29b
diff --git a/test/integration/test-fixtures/image-path-type-change/chimera/b.txt b/test/integration/test-fixtures/image-path-type-change/chimera/b.txt
new file mode 100644
index 00000000..e69de29b