diff --git a/R/course.R b/R/course.R
index 772743717..ce2389576 100644
--- a/R/course.R
+++ b/R/course.R
@@ -529,10 +529,14 @@ top_directory <- function(filenames) {
   in_top <- path_dir(filenames) == "."
   unique_top <- unique(filenames[in_top])
   is_directory <- grepl("/$", unique_top)
-  if (length(unique_top) > 1 || !is_directory) {
-    NA_character_
+  if (length(unique(path_dir(filenames))) == 1 && length(unique_top) == 0) {
+    unique_top <- unique(path_dir(filenames))
   } else {
-    unique_top
+    if (length(unique_top) > 1 || !is_directory) {
+      NA_character_
+    } else {
+      unique_top
+    }
   }
 }
 
diff --git a/tests/testthat/ref/foo-rename.zip b/tests/testthat/ref/foo-rename.zip
new file mode 100644
index 000000000..d8341e925
Binary files /dev/null and b/tests/testthat/ref/foo-rename.zip differ
diff --git a/tests/testthat/ref/foo/file1.txt b/tests/testthat/ref/foo/file1.txt
new file mode 100644
index 000000000..674358ffa
--- /dev/null
+++ b/tests/testthat/ref/foo/file1.txt
@@ -0,0 +1 @@
+I am file1.txt that lives inside /foo
diff --git a/tests/testthat/test-course.R b/tests/testthat/test-course.R
index 0dff96f88..290158a98 100644
--- a/tests/testthat/test-course.R
+++ b/tests/testthat/test-course.R
@@ -106,6 +106,20 @@ test_that("tidy_unzip() deals with loose parts, reports unpack destination", {
   expect_identical(loose_dropbox_files, not_loose_files)
 })
 
+test_that("tidy_unzip() deals with different directory names inside zip file", {
+  tmp <- file_temp(ext = ".zip")
+  fs::file_copy(test_file("foo-rename.zip"), tmp)
+  dest <- tidy_unzip(tmp)
+
+  found <- path_file(dest)
+  foonames <- unzip(test_file("foo-rename.zip"), list=TRUE)$Name
+  expected <- (unique(path_dir(foonames)))
+  fs::dir_delete(dest)
+
+  expect_identical(found, expected)
+})
+
+
 ## helpers ----
 test_that("create_download_url() works", {
   expect_equal(