diff --git a/pygit2/callbacks.py b/pygit2/callbacks.py
index 5a040fbe6..05d02fdd3 100644
--- a/pygit2/callbacks.py
+++ b/pygit2/callbacks.py
@@ -632,7 +632,7 @@ def _checkout_progress_cb(path, completed_steps, total_steps, data: CheckoutCall
     data.checkout_progress(maybe_string(path), completed_steps, total_steps)
 
 
-def _git_checkout_options(callbacks=None, strategy=None, directory=None, paths=None):
+def _git_checkout_options(callbacks=None, strategy=None, directory=None, paths=None, c_checkout_options_ptr=None):
     if callbacks is None:
         payload = CheckoutCallbacks()
     else:
@@ -642,7 +642,10 @@ def _git_checkout_options(callbacks=None, strategy=None, directory=None, paths=N
     handle = ffi.new_handle(payload)
 
     # Create the options struct to pass
-    opts = ffi.new('git_checkout_options *')
+    if not c_checkout_options_ptr:
+        opts = ffi.new('git_checkout_options *')
+    else:
+        opts = c_checkout_options_ptr
     check_error(C.git_checkout_init_options(opts, 1))
 
     # References we need to keep to strings and so forth
@@ -714,23 +717,25 @@ def git_stash_apply_options(callbacks=None, reinstate_index=False, strategy=None
     if callbacks is None:
         callbacks = StashApplyCallbacks()
 
-    # First, set up checkout_options
-    payload = _git_checkout_options(callbacks=callbacks, strategy=strategy, directory=directory, paths=paths)
-    assert payload == callbacks
-
-    # Now set up the rest of stash options
+    # Set up stash options
     # TODO: git_stash_apply_init_options is deprecated (along with a bunch of other git_XXX_init_options functions)
-    stash_options = ffi.new('git_stash_apply_options *')
-    check_error(C.git_stash_apply_init_options(stash_options, 1))
+    stash_apply_options = ffi.new('git_stash_apply_options *')
+    check_error(C.git_stash_apply_init_options(stash_apply_options, 1))
 
     flags = reinstate_index * C.GIT_STASH_APPLY_REINSTATE_INDEX
-    stash_options.flags = flags
+    stash_apply_options.flags = flags
+
+    # Now set up checkout options
+    c_checkout_options_ptr = ffi.addressof(stash_apply_options.checkout_options)
+    payload = _git_checkout_options(callbacks=callbacks, strategy=strategy, directory=directory, paths=paths, c_checkout_options_ptr=c_checkout_options_ptr)
+    assert payload == callbacks
+    assert payload.checkout_options == c_checkout_options_ptr
 
     # Set up stash progress callback if the user has provided their own
     if type(callbacks).stash_apply_progress != StashApplyCallbacks.stash_apply_progress:
-        stash_options.progress_cb = C._stash_apply_progress_cb
-        stash_options.progress_payload = payload._ffi_handle
+        stash_apply_options.progress_cb = C._stash_apply_progress_cb
+        stash_apply_options.progress_payload = payload._ffi_handle
 
     # Give back control
-    payload.stash_options = stash_options
+    payload.stash_apply_options = stash_apply_options
     yield payload
diff --git a/pygit2/repository.py b/pygit2/repository.py
index 13d2f9a82..b33b3d560 100644
--- a/pygit2/repository.py
+++ b/pygit2/repository.py
@@ -1112,7 +1112,7 @@ def stash_apply(self, index=0, **kwargs):
             >>> repo.stash_apply(strategy=GIT_CHECKOUT_ALLOW_CONFLICTS)
         """
         with git_stash_apply_options(**kwargs) as payload:
-            err = C.git_stash_apply(self._repo, index, payload.stash_options)
+            err = C.git_stash_apply(self._repo, index, payload.stash_apply_options)
             payload.check_error(err)
 
     def stash_drop(self, index=0):
@@ -1133,7 +1133,7 @@ def stash_pop(self, index=0, **kwargs):
         For arguments, see Repository.stash_apply().
         """
         with git_stash_apply_options(**kwargs) as payload:
-            err = C.git_stash_pop(self._repo, index, payload.stash_options)
+            err = C.git_stash_pop(self._repo, index, payload.stash_apply_options)
             payload.check_error(err)
 
     #
diff --git a/test/test_repository.py b/test/test_repository.py
index 61bfe1d1c..a5bde8e63 100644
--- a/test/test_repository.py
+++ b/test/test_repository.py
@@ -414,6 +414,40 @@ def stash_apply_progress(self, progress: int):
     assert 1 == len(repo_stashes)
     assert repo_stashes[0].message == "On master: custom stash message"
 
+def test_stash_apply_checkout_options(testrepo):
+    sig = pygit2.Signature(name='Stasher', email='stasher@example.com', time=1641000000, offset=0)
+
+    hello_txt = Path(testrepo.workdir) / 'hello.txt'
+
+    # some changes to working dir
+    with hello_txt.open('w') as f:
+        f.write('stashed content')
+
+    # create the stash
+    testrepo.stash(sig, include_untracked=True, message="custom stash message")
+
+    # define callbacks that raise an InterruptedError when checkout detects a conflict
+    class MyStashApplyCallbacks(pygit2.StashApplyCallbacks):
+        def checkout_notify(self, why, path, baseline, target, workdir):
+            if why == pygit2.GIT_CHECKOUT_NOTIFY_CONFLICT:
+                raise InterruptedError("Applying the stash would create a conflict")
+
+    # overwrite hello.txt so that applying the stash would create a conflict
+    with hello_txt.open('w') as f:
+        f.write('conflicting content')
+
+    # apply the stash with the default (safe) strategy;
+    # the callbacks should detect a conflict on checkout
+    with pytest.raises(InterruptedError):
+        testrepo.stash_apply(strategy=pygit2.GIT_CHECKOUT_SAFE, callbacks=MyStashApplyCallbacks())
+    
+    # hello.txt should be intact
+    with hello_txt.open('r') as f: assert f.read() == 'conflicting content'
+
+    # force apply the stash; this should work
+    testrepo.stash_apply(strategy=pygit2.GIT_CHECKOUT_FORCE, callbacks=MyStashApplyCallbacks())
+    with hello_txt.open('r') as f: assert f.read() == 'stashed content'
+
 
 def test_revert(testrepo):
     master = testrepo.head.peel()