diff --git a/test/blackbox-tests/test-cases/ctypes/directories.t b/test/blackbox-tests/test-cases/ctypes/directories.t
new file mode 100644
index 000000000000..4f040fe7792d
--- /dev/null
+++ b/test/blackbox-tests/test-cases/ctypes/directories.t
@@ -0,0 +1,77 @@
+This test characterizes how the ctypes support deals with directories, in
+particular when relative paths are passed as `-I`.
+
+With `(using ctypes 0.2)`, some commands are executed in workspace root and
+others are executed in the directory where `(ctypes)` is found, so it is
+necessary to pass relative dirs twice. (this prevents vendorability, since this
+requires knowing the path from the workspace root to the current directory).
+
+To test that, we create a binding to `O_RDWR` and `open`, both in the C library.
+These are provided by `fcntl.h`, but instead of using this header, we're
+proxying it through a `lib.h` which should be in the include path for
+compilation to work.
+
+  $ cat > dune-project << EOF
+  > (lang dune 3.4)
+  > (using ctypes 0.2)
+  > EOF
+
+  $ mkdir lib
+
+  $ mk_dune () {
+  > local flags=$1
+  >  cat << EOF
+  > (executable
+  >  (name e)
+  >  (flags :standard -w -27)
+  >  (ctypes
+  >   (build_flags_resolver
+  >    (vendored (c_flags :standard $flags)))
+  >   (external_library_name l)
+  >   (headers (include lib.h))
+  >   (deps lib.h)
+  >   (type_description
+  >    (functor f)
+  >    (instance types))
+  >   (function_description
+  >    (functor f)
+  >    (instance functions))
+  >   (generated_entry_point entry)))
+  > EOF
+  > }
+
+  $ mk_dune "-I lib -I ." > lib/dune
+
+  $ cat > lib/lib.h << EOF
+  > #include <fcntl.h>
+  > EOF
+
+  $ cat > lib/e.ml << EOF
+  > let () = Printf.printf "%d\n" Entry.Types.rdwr
+  > let (_:char Ctypes.ptr -> int -> int) = Entry.Functions.open_
+  > EOF
+
+  $ cat > lib/f.ml << EOF
+  > module Types(F:Ctypes.TYPE) = struct
+  >   open F
+  >   let rdwr = constant "O_RDWR" int
+  > end
+  > 
+  > module Functions(F:Ctypes.FOREIGN) = struct
+  >   open Ctypes
+  >   open F
+  >   let open_ = foreign "open" (ptr char @-> int @-> returning int)
+  > end
+  > EOF
+
+  $ dune build
+
+We ensure that just `-I lib` or `-I .` are not enough on their own.
+
+  $ mk_dune "-I lib" > lib/dune
+  $ dune build > /dev/null 2>&1
+  [1]
+
+  $ mk_dune "-I ." > lib/dune
+  $ dune build > /dev/null 2>&1
+  [1]