diff --git a/CHANGELOG.md b/CHANGELOG.md
index 7e2779c31..042db3bad 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -6,6 +6,10 @@
 
 - If you use a narrow string path interface (for instance, `sentry_options_set_database_path()`) on _Windows_ rather than one of the wide string variants (`sentry_options_set_database_pathw()`), then the expected encoding is now UTF-8. ([#1413](https://github.com/getsentry/sentry-native/pull/1413))
 
+**Features**:
+
+- Support modifying attachments after `sentry_init` on macOS. ([#1429](https://github.com/getsentry/sentry-native/pull/1429))
+
 **Fixes**:
 
 - Add logs flush on crash. This is not available for macOS with the `crashpad` backend. ([#1404](https://github.com/getsentry/sentry-native/pull/1404))
diff --git a/external/crashpad b/external/crashpad
index b160f39e9..8ffbd55a2 160000
--- a/external/crashpad
+++ b/external/crashpad
@@ -1 +1 @@
-Subproject commit b160f39e9cea7b365d963d9e4774e0fa22c03725
+Subproject commit 8ffbd55a2fd8359c66682f7bff70f5f2f9c72f3d
diff --git a/include/sentry.h b/include/sentry.h
index 0548fa667..586e34427 100644
--- a/include/sentry.h
+++ b/include/sentry.h
@@ -42,9 +42,6 @@
  * attachment paths will be resolved according to the current working directory
  * at the time of envelope creation. When adding and removing attachments, they
  * are matched according to their given `path`. No normalization is performed.
- * When using the `crashpad` backend on macOS, the list of attachments that will
- * be added at the time of a hard crash will be frozen at the time of
- * `sentry_init`, and later modifications will not be reflected.
  */
 
 #ifndef SENTRY_H_INCLUDED
diff --git a/src/backends/sentry_backend_crashpad.cpp b/src/backends/sentry_backend_crashpad.cpp
index b8d0069ef..f4ce5b941 100644
--- a/src/backends/sentry_backend_crashpad.cpp
+++ b/src/backends/sentry_backend_crashpad.cpp
@@ -742,7 +742,8 @@ crashpad_backend_prune_database(sentry_backend_t *backend)
     crashpad::PruneCrashReportDatabase(data->db, &condition);
 }
 
-#if defined(SENTRY_PLATFORM_WINDOWS) || defined(SENTRY_PLATFORM_LINUX)
+#if defined(SENTRY_PLATFORM_WINDOWS) || defined(SENTRY_PLATFORM_LINUX)         \
+    || defined(SENTRY_PLATFORM_MACOS)
 static bool
 ensure_unique_path(sentry_attachment_t *attachment)
 {
@@ -835,7 +836,8 @@ sentry__backend_new(void)
     backend->user_consent_changed_func = crashpad_backend_user_consent_changed;
     backend->get_last_crash_func = crashpad_backend_last_crash;
     backend->prune_database_func = crashpad_backend_prune_database;
-#if defined(SENTRY_PLATFORM_WINDOWS) || defined(SENTRY_PLATFORM_LINUX)
+#if defined(SENTRY_PLATFORM_WINDOWS) || defined(SENTRY_PLATFORM_LINUX)         \
+    || defined(SENTRY_PLATFORM_MACOS)
     backend->add_attachment_func = crashpad_backend_add_attachment;
     backend->remove_attachment_func = crashpad_backend_remove_attachment;
 #endif
diff --git a/tests/assertions.py b/tests/assertions.py
index b7c0e0a4e..a09f178b0 100644
--- a/tests/assertions.py
+++ b/tests/assertions.py
@@ -461,11 +461,9 @@ def assert_crashpad_upload(req, expect_attachment=False, expect_view_hierarchy=F
     assert_event_meta(attachments.event, integration="crashpad")
     if expect_attachment:
         assert attachments.cmake_cache > 0
-    else:
-        assert attachments.cmake_cache == -1
-    if expect_attachment and (sys.platform == "win32" or sys.platform == "linux"):
         assert attachments.bytes_bin == b"\xc0\xff\xee"
     else:
+        assert attachments.cmake_cache == -1
         assert attachments.bytes_bin == None
     if expect_view_hierarchy:
         assert_attachment_content_view_hierarchy(attachments.view_hierarchy)
diff --git a/tests/test_integration_crashpad.py b/tests/test_integration_crashpad.py
index 6bec1c279..9b556ad6d 100644
--- a/tests/test_integration_crashpad.py
+++ b/tests/test_integration_crashpad.py
@@ -352,18 +352,10 @@ def test_crashpad_wer_crash(cmake, httpserver, run_args):
         pytest.param(
             ["attach-after-init"],
             {},
-            marks=pytest.mark.skipif(
-                sys.platform == "darwin",
-                reason="crashpad doesn't support dynamic attachments on macOS",
-            ),
         ),
         pytest.param(
             ["attachment", "attach-after-init", "clear-attachments"],
             {},
-            marks=pytest.mark.skipif(
-                sys.platform == "darwin",
-                reason="crashpad doesn't support dynamic attachments on macOS",
-            ),
         ),
     ],
 )