diff --git a/site/src/utils/templateVersion.test.ts b/site/src/utils/templateVersion.test.ts
new file mode 100644
index 0000000000..6e73e027f9
--- /dev/null
+++ b/site/src/utils/templateVersion.test.ts
@@ -0,0 +1,25 @@
+import { TarReader, TarWriter } from "./tar";
+import { createTemplateVersionFileTree } from "./templateVersion";
+
+test("createTemplateVersionFileTree ignores empty path segments", async () => {
+	const writer = new TarWriter();
+	writer.addFolder("files/etc/apt/");
+	writer.addFile(
+		"files/etc/apt/sources.list",
+		"deb http://example.com stable main",
+	);
+
+	const tarFile = await writer.write();
+	const reader = new TarReader();
+	await reader.readFile(tarFile);
+
+	expect(createTemplateVersionFileTree(reader)).toEqual({
+		files: {
+			etc: {
+				apt: {
+					"sources.list": "deb http://example.com stable main",
+				},
+			},
+		},
+	});
+});
diff --git a/site/src/utils/templateVersion.ts b/site/src/utils/templateVersion.ts
index ac0e0d8908..5da96aa302 100644
--- a/site/src/utils/templateVersion.ts
+++ b/site/src/utils/templateVersion.ts
@@ -30,7 +30,7 @@ export const createTemplateVersionFileTree = (
 	for (const file of tarReader.fileInfo) {
 		fileTree = set(
 			fileTree,
-			file.name.split("/"),
+			file.name.split("/").filter((part) => part !== ""),
 			file.type === TarFileTypeCodes.Dir
 				? {}
 				: (tarReader.getTextFile(file.name) as string),