diff --git a/CHANGELOG.md b/CHANGELOG.md
index c823906..c7ba46d 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -3,6 +3,7 @@ nylas-python Changelog
 Unreleased
 ----------
 * Added optional `tracking_options.domain_name` support for custom link and open tracking hostnames in message sends, scheduled sends, drafts, and Transactional Send
+* Added Contact metadata request/response models and `metadata_pair` filtering, with contact webhook compatibility documentation
 
 v6.17.0
 ----------
diff --git a/nylas/models/contacts.py b/nylas/models/contacts.py
index 9ddcc1c..c9fa790 100644
--- a/nylas/models/contacts.py
+++ b/nylas/models/contacts.py
@@ -1,6 +1,6 @@
 from dataclasses import dataclass
 from enum import Enum
-from typing import Optional, List
+from typing import Dict, List, Optional
 from typing_extensions import TypedDict, NotRequired
 
 from dataclasses_json import dataclass_json
@@ -132,6 +132,9 @@ class Contact:
         given_name: The contact's given name.
         job_title: The contact's job title.
         manager_name: The contact's manager name.
+        metadata: Nylas-owned metadata associated with the contact. Metadata is
+            not written to the provider and does not follow a contact if its
+            public ID changes.
         middle_name: The contact's middle name.
         nickname: The contact's nickname.
         notes: The contact's notes.
@@ -158,6 +161,7 @@ class Contact:
     given_name: Optional[str] = None
     job_title: Optional[str] = None
     manager_name: Optional[str] = None
+    metadata: Optional[Dict[str, str]] = None
     middle_name: Optional[str] = None
     nickname: Optional[str] = None
     notes: Optional[str] = None
@@ -286,6 +290,9 @@ class CreateContactRequest(TypedDict):
         given_name: The contact's given name.
         job_title: The contact's job title.
         manager_name: The contact's manager name.
+        metadata: Nylas-owned metadata for the contact. On update, omission or
+            None preserves existing metadata, an object replaces it, and an
+            empty object clears it.
         middle_name: The contact's middle name.
         nickname: The contact's nickname.
         notes: The contact's notes.
@@ -309,6 +316,7 @@ class CreateContactRequest(TypedDict):
     given_name: NotRequired[str]
     job_title: NotRequired[str]
     manager_name: NotRequired[str]
+    metadata: NotRequired[Optional[Dict[str, str]]]
     middle_name: NotRequired[str]
     nickname: NotRequired[str]
     notes: NotRequired[str]
@@ -338,6 +346,9 @@ class ListContactsQueryParams(ListQueryParams):
         source: Return contacts from a specific source.
         group: Return contacts from a specific group.
         recurse: Return contacts from all sub-groups of the specified group.
+        metadata_pair: Filter by one indexed metadata key/value pair. Use one
+            of key1 through key5. This cannot be combined with provider-side
+            contact filters; pagination parameters are supported.
         select (NotRequired[str]): Comma-separated list of fields to return in the response.
             This allows you to receive only the portion of object data that you're interested in.
         limit (NotRequired[int]): The maximum number of objects to return.
@@ -351,6 +362,7 @@ class ListContactsQueryParams(ListQueryParams):
     source: NotRequired[SourceType]
     group: NotRequired[str]
     recurse: NotRequired[bool]
+    metadata_pair: NotRequired[Dict[str, str]]
 
 
 class GroupType(str, Enum):
diff --git a/nylas/models/webhooks.py b/nylas/models/webhooks.py
index 7cbee4a..982e130 100644
--- a/nylas/models/webhooks.py
+++ b/nylas/models/webhooks.py
@@ -10,7 +10,13 @@
 
 
 class WebhookTriggers(str, Enum):
-    """Enum representing the available webhook triggers."""
+    """
+    Enum representing the available webhook triggers.
+
+    Native iCloud contacts support CONTACT_UPDATED and CONTACT_DELETED. Yahoo
+    contacts support neither trigger, including for changes made through the
+    Nylas API. There is no CONTACT_CREATED trigger.
+    """
     BOOKING_CREATED = "booking.created"
     BOOKING_PENDING = "booking.pending"
     BOOKING_RESCHEDULED = "booking.rescheduled"
diff --git a/tests/handler/test_http_client.py b/tests/handler/test_http_client.py
index 416b357..7564e23 100644
--- a/tests/handler/test_http_client.py
+++ b/tests/handler/test_http_client.py
@@ -170,6 +170,17 @@ def test_build_query_params(self, patched_version_and_sys):
             == "https://test.nylas.com/foo?foo=bar&list=a&list=b&list=c&map=key1:value1&map=key2:value2"
         )
 
+    def test_build_contact_metadata_pair_query_param(self):
+        url = _build_query_params(
+            base_url="https://test.nylas.com/v3/grants/abc-123/contacts",
+            query_params={"metadata_pair": {"key1": "sync_eligible"}},
+        )
+
+        assert (
+            url
+            == "https://test.nylas.com/v3/grants/abc-123/contacts?metadata_pair=key1:sync_eligible"
+        )
+
     def test_execute_download_request(self, http_client, patched_request):
         response = http_client._execute_download_request(
             path="/foo",
diff --git a/tests/resources/test_contacts.py b/tests/resources/test_contacts.py
index c55cff0..41b212b 100644
--- a/tests/resources/test_contacts.py
+++ b/tests/resources/test_contacts.py
@@ -24,6 +24,7 @@ def test_contact_deserialization(self):
             "im_addresses": [{"type": "other", "im_address": "myjabberaddress"}],
             "job_title": "Software Engineer",
             "manager_name": "Bill",
+            "metadata": {"key1": "sync_eligible"},
             "middle_name": "Jacob",
             "nickname": "JD",
             "notes": "Loves ramen",
@@ -64,6 +65,7 @@ def test_contact_deserialization(self):
         ]
         assert contact.job_title == "Software Engineer"
         assert contact.manager_name == "Bill"
+        assert contact.metadata == {"key1": "sync_eligible"}
         assert contact.middle_name == "Jacob"
         assert contact.nickname == "JD"
         assert contact.notes == "Loves ramen"
@@ -112,6 +114,23 @@ def test_list_contacts_with_query_params(self, http_client_list_response):
             overrides=None,
         )
 
+    def test_list_contacts_with_metadata_pair(self, http_client_list_response):
+        contacts = Contacts(http_client_list_response)
+
+        contacts.list(
+            identifier="abc-123",
+            query_params={"metadata_pair": {"key1": "sync_eligible"}},
+        )
+
+        http_client_list_response._execute.assert_called_once_with(
+            "GET",
+            "/v3/grants/abc-123/contacts",
+            None,
+            {"metadata_pair": {"key1": "sync_eligible"}},
+            None,
+            overrides=None,
+        )
+
     def test_list_contacts_with_select_param(self, http_client_list_response):
         contacts = Contacts(http_client_list_response)
 
@@ -219,6 +238,7 @@ def test_create_contact(self, http_client_response):
             "given_name": "John",
             "surname": "Doe",
             "company_name": "Nylas",
+            "metadata": {"key1": "sync_eligible"},
         }
 
         contacts.create(identifier="abc-123", request_body=request_body)
@@ -238,6 +258,7 @@ def test_update_contact(self, http_client_response):
             "given_name": "John",
             "surname": "Doe",
             "company_name": "Nylas",
+            "metadata": {},
         }
 
         contacts.update(
diff --git a/tests/resources/test_webhooks.py b/tests/resources/test_webhooks.py
index 159a94d..bc5e810 100644
--- a/tests/resources/test_webhooks.py
+++ b/tests/resources/test_webhooks.py
@@ -5,6 +5,11 @@
 
 
 class TestWebhooks:
+    def test_contact_webhook_contract(self):
+        assert WebhookTriggers.CONTACT_UPDATED.value == "contact.updated"
+        assert WebhookTriggers.CONTACT_DELETED.value == "contact.deleted"
+        assert "contact.created" not in {trigger.value for trigger in WebhookTriggers}
+
     def test_webhook_deserialization(self, http_client):
         webhook_json = {
             "id": "UMWjAjMeWQ4D8gYF2moonK4486",