diff --git a/mypy.ini b/mypy.ini
--- a/mypy.ini
+++ b/mypy.ini
@@ -22,3 +22,6 @@
 
 [mypy-systemd.daemon.*]
 ignore_missing_imports = True
+
+[mypy-tenacity.*]
+ignore_missing_imports = True
diff --git a/requirements.txt b/requirements.txt
--- a/requirements.txt
+++ b/requirements.txt
@@ -3,4 +3,5 @@
 # dependency lines, see https://pip.readthedocs.org/en/1.1/requirements.html
 confluent-kafka
 msgpack
+tenacity
 vcversioner
diff --git a/swh/journal/replay.py b/swh/journal/replay.py
--- a/swh/journal/replay.py
+++ b/swh/journal/replay.py
@@ -13,6 +13,8 @@
 except ImportError:
     notify = None
 
+from tenacity import retry, stop_after_attempt, wait_random_exponential
+
 from swh.core.statsd import statsd
 from swh.model.identifiers import normalize_timestamp
 from swh.model.hashutil import hash_to_hex
@@ -322,6 +324,14 @@
     return len(obj)
 
 
+@retry(stop=stop_after_attempt(3),
+       reraise=True,
+       wait=wait_random_exponential(multiplier=1, max=60))
+def obj_in_objstorage(obj_id, dst):
+    """Check if an object is already in an objstorage, tenaciously"""
+    return obj_id in dst
+
+
 def process_replay_objects_content(
         all_objects: Dict[str, List[dict]],
         *,
@@ -401,7 +411,7 @@
                              hash_to_hex(obj_id))
                 statsd.increment(CONTENT_OPERATIONS_METRIC,
                                  tags={"decision": "excluded"})
-            elif check_dst and obj_id in dst:
+            elif check_dst and obj_in_objstorage(obj_id, dst):
                 nb_skipped += 1
                 logger.debug('skipped %s (in dst)', hash_to_hex(obj_id))
                 statsd.increment(CONTENT_OPERATIONS_METRIC,
diff --git a/swh/journal/tests/test_cli.py b/swh/journal/tests/test_cli.py
--- a/swh/journal/tests/test_cli.py
+++ b/swh/journal/tests/test_cli.py
@@ -3,6 +3,7 @@
 # License: GNU General Public License version 3, or any later version
 # See top-level LICENSE file for more information
 
+from collections import Counter
 import functools
 import logging
 import re
@@ -338,3 +339,59 @@
     for (sha1, content) in contents.items():
         assert sha1 in objstorages['dst'], sha1
         assert objstorages['dst'].get(sha1) == content
+
+
+@_patch_objstorages(['src', 'dst'])
+def test_replay_content_check_dst_retry(
+        objstorages,
+        storage,
+        kafka_prefix: str,
+        kafka_consumer_group: str,
+        kafka_server: Tuple[Popen, int]):
+    (_, kafka_port) = kafka_server
+    kafka_prefix += '.swh.journal.objects'
+
+    contents = _fill_objstorage_and_kafka(
+        kafka_port, kafka_prefix, objstorages)
+
+    class FlakyMemoryObjStorage(InMemoryObjStorage):
+        def __init__(self, *args, **kwargs):
+            state = kwargs.pop('state')
+            super().__init__(*args, **kwargs)
+            if state:
+                self.state = state
+            self.contains_failed = Counter()
+
+        def __contains__(self, id):
+            if self.contains_failed[id] == 0:
+                self.contains_failed[id] += 1
+                raise ValueError('This contains is flaky')
+
+            return super().__contains__(id)
+
+    for i, (sha1, content) in enumerate(contents.items()):
+        if i >= NUM_CONTENTS_DST:
+            break
+
+        objstorages['dst'].add(content, obj_id=sha1)
+
+    dst_state = objstorages['dst'].state
+    flaky_objstorage = FlakyMemoryObjStorage(state=dst_state)
+    objstorages['dst'] = flaky_objstorage
+    dst_contains_failed = flaky_objstorage.contains_failed
+
+    result = invoke(False, [
+        'content-replay',
+        '--broker', '127.0.0.1:%d' % kafka_port,
+        '--group-id', kafka_consumer_group,
+        '--prefix', kafka_prefix,
+        '--max-messages', str(NUM_CONTENTS),
+        '--check-dst',
+    ])
+    expected = r'Done.\n'
+    assert result.exit_code == 0, result.output
+    assert re.fullmatch(expected, result.output, re.MULTILINE), result.output
+
+    for (sha1, content) in contents.items():
+        assert dst_contains_failed[sha1] >= 0
+        assert dst_state[sha1] == content