diff --git a/pyproject.toml b/pyproject.toml
index 6395c88..30ab036 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -1,6 +1,6 @@
 [tool.poetry]
 name = "tap-mongodb"
-version = "2.3.3"
+version = "2.4.0"
 description = "`tap-mongodb` is a Singer tap for MongoDB and AWS DocumentDB, built with the Meltano Singer SDK."
 readme = "README.md"
 authors = ["Matt Menzenski"]
diff --git a/tap_mongodb/connector.py b/tap_mongodb/connector.py
index 366192a..627d141 100644
--- a/tap_mongodb/connector.py
+++ b/tap_mongodb/connector.py
@@ -2,7 +2,7 @@
 
 import sys
 from logging import Logger, getLogger
-from typing import Any, Dict, List, Optional
+from typing import Any, Dict, List, Optional, Tuple, TypeAlias
 
 from pymongo import MongoClient
 from pymongo.database import Database
@@ -17,6 +17,9 @@
     from functools import cached_property
 
 
+MongoVersion: TypeAlias = Tuple[int, int]
+
+
 class MongoDBConnector:
     """MongoDB/DocumentDB connector class"""
 
@@ -34,6 +37,7 @@ def __init__(  # pylint: disable=too-many-arguments
         self._datetime_conversion: str = datetime_conversion.upper()
         self._prefix: Optional[str] = prefix
         self._logger: Logger = getLogger(__name__)
+        self._version: Optional[MongoVersion] = None
 
     @cached_property
     def mongo_client(self) -> MongoClient:
@@ -42,7 +46,9 @@ def mongo_client(self) -> MongoClient:
             self._connection_string, datetime_conversion=self._datetime_conversion, **self._options
         )
         try:
-            client.server_info()
+            server_info: Dict[str, Any] = client.server_info()
+            version_array: List[int] = server_info["versionArray"]
+            self._version = (version_array[0], version_array[1])
         except Exception as exception:
             self._logger.exception("Could not connect to MongoDB")
             raise RuntimeError("Could not connect to MongoDB") from exception
@@ -53,6 +59,11 @@ def database(self) -> Database:
         """Provide a Database instance."""
         return self.mongo_client[self._db_name]
 
+    @property
+    def version(self) -> Optional[MongoVersion]:
+        """Returns the MongoVersion that is being used."""
+        return self._version
+
     def get_fully_qualified_name(
         self,
         collection_name: str,
diff --git a/tap_mongodb/streams.py b/tap_mongodb/streams.py
index 2232920..21d0bf0 100644
--- a/tap_mongodb/streams.py
+++ b/tap_mongodb/streams.py
@@ -218,7 +218,13 @@ def get_records(self, context: dict | None) -> Iterable[dict]:
             change_stream_options = {"full_document": "updateLookup"}
             if bookmark is not None and bookmark != DEFAULT_START_DATE:
                 self.logger.debug(f"using bookmark: {bookmark}")
-                change_stream_options["resume_after"] = {"_data": bookmark}
+                # if on mongo version 4.2 or above, use start_after instead of resume_after, as the former will
+                # gracefully open a new change stream if the resume token's event is not present in the oplog, while
+                # the latter will error in that scenario.
+                if self._connector.version >= (4, 2):
+                    change_stream_options["start_after"] = {"_data": bookmark}
+                else:
+                    change_stream_options["resume_after"] = {"_data": bookmark}
             operation_types_allowlist: set = set(self.config.get("operation_types"))
             has_seen_a_record: bool = False
             keep_open: bool = True
@@ -245,7 +251,8 @@ def get_records(self, context: dict | None) -> Iterable[dict]:
                             f"Unable to enable change streams on collection {collection.name}"
                         ) from operation_failure
                 elif (
-                    operation_failure.code == 286
+                    self._connector.version < (4, 2)
+                    and operation_failure.code == 286
                     and "as the resume point may no longer be in the oplog." in operation_failure.details["errmsg"]
                 ):
                     self.logger.warning("Unable to resume change stream from resume token. Resetting resume token.")
@@ -265,7 +272,8 @@ def get_records(self, context: dict | None) -> Iterable[dict]:
                         record = change_stream.try_next()
                     except OperationFailure as operation_failure:
                         if (
-                            operation_failure.code == 286
+                            self._connector.version < (4, 2)
+                            and operation_failure.code == 286
                             and "as the resume point may no longer be in the oplog."
                             in operation_failure.details["errmsg"]
                         ):