diff --git a/CHANGELOG.md b/CHANGELOG.md
index ee6f06fa..bcba330d 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -9,7 +9,7 @@ The intended audience of this file is for py42 consumers -- as such, changes tha
 how a consumer would use the library (e.g. adding unit tests, updating documentation, etc) are not captured here.
 
 
-## 1.16.3 - 2023-02-01
+## 1.16.5 - 2023-02-01
 
 ### Fixed
 
diff --git a/src/code42cli/__version__.py b/src/code42cli/__version__.py
index 67f76446..9e1406d5 100644
--- a/src/code42cli/__version__.py
+++ b/src/code42cli/__version__.py
@@ -1 +1 @@
-__version__ = "1.16.4"
+__version__ = "1.16.5"
diff --git a/src/code42cli/cmds/securitydata.py b/src/code42cli/cmds/securitydata.py
index 03c637bc..0a0a2b77 100644
--- a/src/code42cli/cmds/securitydata.py
+++ b/src/code42cli/cmds/securitydata.py
@@ -513,6 +513,8 @@ def send_to(
     if state.profile.use_v2_file_events != "True":
         deprecation_warning(DEPRECATION_TEXT)
 
+    flatten = format in (OutputFormat.TABLE, OutputFormat.CSV)
+
     if use_checkpoint:
         cursor = _get_file_event_cursor_store(state.profile.name)
         checkpoint = _handle_timestamp_checkpoint(cursor.get(use_checkpoint), state)
@@ -520,7 +522,8 @@ def send_to(
         if state.profile.use_v2_file_events == "True":
 
             def checkpoint_func(event):
-                cursor.replace(use_checkpoint, event["event.id"])
+                event_id = event["event.id"] if flatten else event["event"]["id"]
+                cursor.replace(use_checkpoint, event_id)
 
         else: