diff --git a/linodecli/plugins/obj/__init__.py b/linodecli/plugins/obj/__init__.py
index 6952487f9..ecbd39456 100644
--- a/linodecli/plugins/obj/__init__.py
+++ b/linodecli/plugins/obj/__init__.py
@@ -15,6 +15,7 @@
 from math import ceil
 from typing import List, Optional
 
+from packaging import version
 from pytimeparse import parse as parse_time
 from rich import print as rprint
 from rich.table import Table
@@ -32,6 +33,7 @@
     ENV_ACCESS_KEY_NAME,
     ENV_SECRET_KEY_NAME,
     INCOMING_DATE_FORMAT,
+    MIN_BOTOCORE_VERSION,
     MULTIPART_UPLOAD_CHUNK_SIZE_DEFAULT,
     NO_ACCESS_ERROR,
     NO_SCOPES_ERROR,
@@ -59,6 +61,7 @@
 
 try:
     import boto3
+    import botocore
     from botocore.config import Config
     from botocore.exceptions import ClientError
 
@@ -68,6 +71,29 @@
 
 
 CLUSTER_KEY = "cluster"
+
+
+def _check_botocore_version():
+    """
+    Exits with an upgrade hint if the installed botocore is too old for the
+    options the S3 client is configured with.
+    """
+    if version.parse(botocore.__version__) >= version.parse(
+        MIN_BOTOCORE_VERSION
+    ):
+        return
+
+    print(
+        f"This plugin requires boto3 {MIN_BOTOCORE_VERSION} or later, but "
+        f"botocore {botocore.__version__} is installed. Please upgrade it by "
+        "running 'pip3 install --upgrade boto3', or reinstall the CLI with "
+        "its Object Storage dependencies: "
+        "'pip3 install --upgrade \"linode-cli[obj]\"'",
+        file=sys.stderr,
+    )
+    sys.exit(ExitCodes.REQUEST_FAILED)
+
+
 KEY_CLEANUP_ENABLED_KEY = "key-cleanup-enabled"
 KEY_LIFESPAN_KEY = "key-lifespan"
 KEY_ROTATION_PERIOD_KEY = "key-rotation-period"
@@ -430,6 +456,8 @@ def call(
             ExitCodes.REQUEST_FAILED
         )  # requirements not met - we can't go on
 
+    _check_botocore_version()
+
     parser = get_obj_args_parser()
     parsed, args = parser.parse_known_args(args)
 
diff --git a/linodecli/plugins/obj/config.py b/linodecli/plugins/obj/config.py
index 0e287f56c..a879ef73f 100644
--- a/linodecli/plugins/obj/config.py
+++ b/linodecli/plugins/obj/config.py
@@ -28,6 +28,10 @@
 # for help commands
 PLUGIN_BASE = "linode-cli obj"
 
+# the oldest botocore that accepts the checksum options the S3 client is
+# configured with; boto3 releases use the matching botocore version
+MIN_BOTOCORE_VERSION = "1.36.0"
+
 columns = shutil.get_terminal_size(fallback=(80, 24)).columns
 PROGRESS_BAR_WIDTH = columns - 20 if columns > 30 else columns
 
diff --git a/tests/unit/test_plugin_obj.py b/tests/unit/test_plugin_obj.py
index 608508099..affb80812 100644
--- a/tests/unit/test_plugin_obj.py
+++ b/tests/unit/test_plugin_obj.py
@@ -1,9 +1,11 @@
 import time
-from unittest.mock import patch
+from unittest.mock import Mock, patch
 
+import pytest
 from pytest import CaptureFixture
 
 from linodecli import CLI, plugins
+from linodecli.exit_codes import ExitCodes
 from linodecli.plugins import obj
 from linodecli.plugins.obj import get_obj_args_parser, helpers, print_help
 
@@ -336,3 +338,40 @@ def call_operation_side_effect(resource, action, *args, **kwargs):
         assert (
             not delete_calls
         ), "Cleanup should not be performed when key-cleanup-enabled is False"
+
+
+@pytest.mark.parametrize("botocore_version", ["1.36.0", "1.43.1"])
+def test_check_botocore_version_accepts_supported(botocore_version: str):
+    with patch.object(obj.botocore, "__version__", botocore_version):
+        obj._check_botocore_version()
+
+
+def test_check_botocore_version_rejects_outdated(capsys: CaptureFixture):
+    with (
+        patch.object(obj.botocore, "__version__", "1.35.99"),
+        pytest.raises(SystemExit) as exc,
+    ):
+        obj._check_botocore_version()
+
+    assert exc.value.code == ExitCodes.REQUEST_FAILED
+    err = capsys.readouterr().err
+    assert "requires boto3 1.36.0 or later" in err
+    assert "botocore 1.35.99 is installed" in err
+    assert "pip3 install --upgrade boto3" in err
+
+
+def test_obj_action_with_outdated_botocore_exits_before_client():
+    command = Mock()
+    with (
+        patch.object(obj.botocore, "__version__", "1.35.99"),
+        patch("linodecli.plugins.obj.CLI") as MockCLI,
+        patch.dict(obj.COMMAND_MAP, {"ls": command}),
+        pytest.raises(SystemExit) as exc,
+    ):
+        obj.call(
+            ["ls", "bucket"],
+            plugins.PluginContext("12345", MockCLI.return_value),
+        )
+
+    assert exc.value.code == ExitCodes.REQUEST_FAILED
+    command.assert_not_called()