diff --git a/spacy/tests/regression/test_issue3345.py b/spacy/tests/regression/test_issue3345.py
new file mode 100644
index 000000000..7b1f41fbf
--- /dev/null
+++ b/spacy/tests/regression/test_issue3345.py
@@ -0,0 +1,27 @@
+"""Test interaction between preset entities and sentence boundaries in NER."""
+import spacy
+from spacy.tokens import Doc
+from spacy.pipeline import EntityRuler, EntityRecognizer
+
+
+@pytest.mark.xfail
+def test_issue3345():
+    """Test case where preset entity crosses sentence boundary."""
+    nlp = spacy.blank("en")
+    doc = Doc(nlp.vocab, words=["I", "live", "in", "New", "York"])
+    doc[4].is_sent_start = True
+
+    ruler = EntityRuler(nlp, patterns=[{"label": "GPE", "pattern": "New York"}])
+    ner = EntityRecognizer(doc.vocab)
+    # Add the OUT action. I wouldn't have thought this would be necessary...
+    ner.moves.add_action(5, "")
+    ner.add_label("GPE")
+
+    doc = ruler(doc)
+    # Get into the state just before "New"
+    state = ner.moves.init_batch([doc])[0]
+    ner.moves.apply_transition(state, "O")
+    ner.moves.apply_transition(state, "O")
+    ner.moves.apply_transition(state, "O")
+    # Check that B-GPE is valid.
+    assert ner.moves.is_valid(state, "B-GPE")