diff --git a/src/sentry_database.c b/src/sentry_database.c
index 81646410f..32cf8ba57 100644
--- a/src/sentry_database.c
+++ b/src/sentry_database.c
@@ -103,6 +103,13 @@ static bool
 write_envelope(const sentry_path_t *path, const sentry_envelope_t *envelope)
 {
     sentry_uuid_t event_id = sentry__envelope_get_event_id(envelope);
+
+    // Generate a random UUID for the filename if the envelope has no event_id
+    // this avoids collisions on NIL-UUIDs
+    if (sentry_uuid_is_nil(&event_id)) {
+        event_id = sentry_uuid_new_v4();
+    }
+
     char *envelope_filename = sentry__uuid_as_filename(&event_id, ".envelope");
     if (!envelope_filename) {
         return false;
diff --git a/tests/__init__.py b/tests/__init__.py
index 36fb648e2..710405bf0 100644
--- a/tests/__init__.py
+++ b/tests/__init__.py
@@ -70,6 +70,21 @@ def split_log_request_cond(httpserver_log, cond):
     )
 
 
+def extract_request(httpserver_log, cond):
+    """
+    Extract a request matching the condition from the httpserver log.
+    Returns (matching_request, remaining_log_entries)
+
+    The remaining_log_entries preserves the original format so it can be
+    chained with subsequent extract_request calls.
+    """
+    for i, entry in enumerate(httpserver_log):
+        if cond(entry[0].get_data()):
+            others = [httpserver_log[j] for j in range(len(httpserver_log)) if j != i]
+            return (entry[0], others)
+    return (None, httpserver_log)
+
+
 def run(cwd, exe, args, expect_failure=False, env=None, **kwargs):
     if env is None:
         env = dict(os.environ)
diff --git a/tests/test_integration_crashpad.py b/tests/test_integration_crashpad.py
index 6bec1c279..0a501dd7d 100644
--- a/tests/test_integration_crashpad.py
+++ b/tests/test_integration_crashpad.py
@@ -11,6 +11,7 @@
     run,
     Envelope,
     split_log_request_cond,
+    extract_request,
     is_session_envelope,
     is_logs_envelope,
     is_feedback_envelope,
@@ -614,6 +615,42 @@ def test_crashpad_logs_on_crash(cmake, httpserver):
     assert_logs(logs_envelope, 1)
 
 
+@pytest.mark.skipif(not flushes_state, reason="test needs state flushing")
+def test_crashpad_logs_and_session_on_crash(cmake, httpserver):
+    tmp_path = cmake(["sentry_example"], {"SENTRY_BACKEND": "crashpad"})
+
+    env = dict(os.environ, SENTRY_DSN=make_dsn(httpserver))
+    httpserver.expect_oneshot_request("/api/123456/minidump/").respond_with_data("OK")
+    httpserver.expect_request("/api/123456/envelope/").respond_with_data("OK")
+
+    with httpserver.wait(timeout=10) as waiting:
+        run(
+            tmp_path,
+            "sentry_example",
+            ["log", "enable-logs", "capture-log", "crash", "start-session"],
+            expect_failure=True,
+            env=env,
+        )
+
+    assert waiting.result
+
+    run(tmp_path, "sentry_example", ["log", "no-setup"], env=env)
+
+    # we expect 1 envelope with the log, 1 for the crash, and 1 for the session
+    assert len(httpserver.log) == 3
+
+    logs_request, remaining = extract_request(httpserver.log, is_logs_envelope)
+    session_request, remaining = extract_request(remaining, is_session_envelope)
+    multipart = remaining[0][0]  # The crash/minidump
+
+    logs_envelope = Envelope.deserialize(logs_request.get_data())
+    assert logs_envelope is not None
+    assert_logs(logs_envelope, 1)
+
+    session_envelope = Envelope.deserialize(session_request.get_data())
+    assert session_envelope is not None
+
+
 def test_disable_backend(cmake, httpserver):
     tmp_path = cmake(["sentry_example"], {"SENTRY_BACKEND": "crashpad"})