diff --git a/tests/channels/test_email_channel.py b/tests/channels/test_email_channel.py
index 4341dc5b..98343522 100644
--- a/tests/channels/test_email_channel.py
+++ b/tests/channels/test_email_channel.py
@@ -132,6 +132,69 @@ def test_fetch_new_messages_skips_self_sent_email_and_marks_seen(monkeypatch) ->
     assert items_again == []
 
 
+@pytest.mark.parametrize(
+    "config_override,from_header",
+    [
+        # Only smtp_username matches — simulates an SMTP relay where
+        # outbound From gets rewritten to the SMTP login identity.
+        (
+            {"from_address": "", "smtp_username": "bot@example.com", "imap_username": "other@imap.com"},
+            "bot@example.com",
+        ),
+        # Only imap_username matches — simulates mailbox-based identity
+        # with no explicit from_address set.
+        (
+            {"from_address": "", "smtp_username": "other@smtp.com", "imap_username": "bot@example.com"},
+            "bot@example.com",
+        ),
+        # Case-insensitive: inbound From arrives upper-cased.
+        (
+            {"from_address": "bot@example.com", "smtp_username": "other@smtp.com", "imap_username": "other@imap.com"},
+            "BOT@EXAMPLE.COM",
+        ),
+    ],
+    ids=["smtp_username_only", "imap_username_only", "case_insensitive"],
+)
+def test_fetch_new_messages_skips_self_sent_across_identity_sources(
+    monkeypatch, config_override, from_header
+) -> None:
+    """Self-address detection must fire when any of from_address / smtp_username /
+    imap_username matches, and must be case-insensitive."""
+    raw = _make_raw_email(from_addr=from_header, subject="Loop test")
+
+    class FakeIMAP:
+        def __init__(self) -> None:
+            self.store_calls: list[tuple[bytes, str, str]] = []
+
+        def login(self, _user: str, _pw: str):
+            return "OK", [b"logged in"]
+
+        def select(self, _mailbox: str):
+            return "OK", [b"1"]
+
+        def search(self, *_args):
+            return "OK", [b"1"]
+
+        def fetch(self, _imap_id: bytes, _parts: str):
+            return "OK", [(b"1 (UID 123 BODY[] {200})", raw), b")"]
+
+        def store(self, imap_id: bytes, op: str, flags: str):
+            self.store_calls.append((imap_id, op, flags))
+            return "OK", [b""]
+
+        def logout(self):
+            return "BYE", [b""]
+
+    fake = FakeIMAP()
+    monkeypatch.setattr("nanobot.channels.email.imaplib.IMAP4_SSL", lambda _h, _p: fake)
+
+    channel = EmailChannel(_make_config(**config_override), MessageBus())
+    items = channel._fetch_new_messages()
+
+    assert items == []
+    assert fake.store_calls == [(b"1", "+FLAGS", "\\Seen")]
+
+
 def test_fetch_new_messages_retries_once_when_imap_connection_goes_stale(monkeypatch) -> None:
     raw = _make_raw_email(subject="Invoice", body="Please pay")
     fail_once = {"pending": True}