diff --git a/chrome/content/zotero/xpcom/attachments.js b/chrome/content/zotero/xpcom/attachments.js
index fb3de655e..20d07a4ad 100644
--- a/chrome/content/zotero/xpcom/attachments.js
+++ b/chrome/content/zotero/xpcom/attachments.js
@@ -882,14 +882,15 @@ Zotero.Attachments = new function(){
 		}
 		
 		if (Zotero.File.directoryContains(basePath, path)) {
-			basePath = OS.Path.normalize(basePath);
-			path = OS.Path.normalize(path);
-			path = this.BASE_PATH_PLACEHOLDER
-				+ path.substr(basePath.length + 1)
-				// Since stored paths can be synced to other platforms, use
-				// forward slashes for consistency. resolveRelativePath() will
-				// convert to the appropriate platform-specific slash on use.
-				.replace(/\\/g, "/");
+			// Since stored paths can be synced to other platforms, use forward slashes for consistency.
+			// resolveRelativePath() will convert to the appropriate platform-specific slash on use.
+			basePath = OS.Path.normalize(basePath).replace(/\\/g, "/");
+			path = OS.Path.normalize(path).replace(/\\/g, "/");
+			// Normalize D:\ vs. D:\foo
+			if (!basePath.endsWith('/')) {
+				basePath += '/';
+			}
+			path = this.BASE_PATH_PLACEHOLDER + path.substr(basePath.length)
 		}
 		
 		return path;
diff --git a/test/tests/attachmentsTest.js b/test/tests/attachmentsTest.js
index ce2a9fffb..c9f885606 100644
--- a/test/tests/attachmentsTest.js
+++ b/test/tests/attachmentsTest.js
@@ -210,6 +210,12 @@ describe("Zotero.Attachments", function() {
 	});
 	
 	describe("#getBaseDirectoryRelativePath()", function () {
+		it("should handle base directory at Windows drive root", function () {
+			Zotero.Prefs.set('baseAttachmentPath', "C:\\");
+			var path = Zotero.Attachments.getBaseDirectoryRelativePath("C:\\file.txt");
+			assert.equal(path, Zotero.Attachments.BASE_PATH_PLACEHOLDER + "file.txt");
+		});
+		
 		it("should convert backslashes to forward slashes", function () {
 			Zotero.Prefs.set('baseAttachmentPath', "C:\\foo\\bar");
 			var path = Zotero.Attachments.getBaseDirectoryRelativePath("C:\\foo\\bar\\test\\file.txt");