diff --git a/chrome/content/zotero/xpcom/file.js b/chrome/content/zotero/xpcom/file.js
index b9e20f0df2..41d7709138 100644
--- a/chrome/content/zotero/xpcom/file.js
+++ b/chrome/content/zotero/xpcom/file.js
@@ -102,7 +102,9 @@ Zotero.File = new function () {
 			}
 		}
 		catch (e) {
-			if (e.becauseNoSuchFile) {}
+			// A missing file, or a filename too long for the filesystem, might still have
+			// an existing parent directory, so continue below
+			if (e.becauseNoSuchFile || e.message?.includes('NS_ERROR_FILE_NAME_TOO_LONG')) {}
 			// A path that can't be parsed (e.g., a POSIX-style path on Windows) doesn't
 			// exist either
 			else if (e.message?.includes('NS_ERROR_FILE_UNRECOGNIZED_PATH')) {
diff --git a/test/tests/fileTest.js b/test/tests/fileTest.js
index 229ad8bace..c7412b288a 100644
--- a/test/tests/fileTest.js
+++ b/test/tests/fileTest.js
@@ -199,6 +199,14 @@ describe("Zotero.File", function () {
 			assert.equal(closest, tmpDir);
 		});
 		
+		it("should return parent directory for a filename too long for the filesystem", async function () {
+			var tmpDir = await getTempDirectory();
+			var closest = await Zotero.File.getClosestDirectory(
+				OS.Path.join(tmpDir, 'a'.repeat(1000) + '.pdf')
+			);
+			assert.equal(closest, tmpDir);
+		});
+		
 		it("should return false for a path that doesn't exist at all", async function () {
 			assert.isFalse(await Zotero.File.getClosestDirectory('/a/b/c'));
 		});