diff --git a/flytekit/bin/entrypoint.py b/flytekit/bin/entrypoint.py
index 93cd3e3846..911b4debb9 100644
--- a/flytekit/bin/entrypoint.py
+++ b/flytekit/bin/entrypoint.py
@@ -3,6 +3,7 @@
 import datetime
 import os
 import pathlib
+import re
 import signal
 import subprocess
 import sys
@@ -10,6 +11,7 @@
 import textwrap
 import time
 import traceback
+import typing
 import uuid
 import warnings
 from sys import exit
@@ -398,6 +400,66 @@ def get_one_of(*args) -> str:
     return ""
 
 
+_CHECKPOINT_ATTEMPT_RE = re.compile(r"(.*)-dn0-(\d+)(/_flytecheckpoints/.*)$")
+
+
+def _build_checkpoint_src_list(
+    checkpoint_path: str,
+    prev_checkpoint: typing.Optional[str],
+) -> typing.List[str]:
+    """Build an ordered list of previous checkpoint paths to try during restore.
+
+    Flyte Propeller passes a single ``prev_checkpoint`` pointing at attempt N-1.
+    If that attempt was killed before writing a checkpoint the chain breaks.
+    This function generates paths for *all* previous attempts (N-1 … 0) so the
+    checkpointer can walk back and find the most recent successful one.
+
+    The checkpoint path pattern is:
+        ``<prefix>-dn0-{attempt}/_flytecheckpoints/``
+
+    If we cannot parse the pattern we fall back to ``[prev_checkpoint]``.
+
+    Args:
+        checkpoint_path: The checkpoint *destination* for the current attempt.
+        prev_checkpoint: The single previous checkpoint path from Propeller (may be None).
+
+    Returns:
+        A list of checkpoint source paths ordered most-recent-attempt first.
+    """
+    if not checkpoint_path:
+        return [prev_checkpoint] if prev_checkpoint else []
+
+    m = _CHECKPOINT_ATTEMPT_RE.search(checkpoint_path)
+    if not m:
+        # Cannot parse — fall back to the single prev_checkpoint from Propeller
+        return [prev_checkpoint] if prev_checkpoint else []
+
+    prefix, current_attempt_str, suffix = m.group(1), m.group(2), m.group(3)
+    current_attempt = int(current_attempt_str)
+
+    if current_attempt == 0:
+        # First attempt — nothing to walk back to
+        return []
+
+    # Build paths N-1, N-2, … 0 using the same prefix structure.
+    # NOTE: The prefix (including the hash) may differ across attempts because
+    # Propeller computes it per-attempt.  We use the *current* attempt's prefix
+    # as the best guess — the hash typically stays the same within one execution.
+    # If Propeller provided prev_checkpoint, keep it first because its prefix is
+    # guaranteed correct for attempt N-1.
+    srcs: typing.List[str] = []
+    if prev_checkpoint:
+        srcs.append(prev_checkpoint)
+
+    for attempt in range(current_attempt - 1, -1, -1):
+        candidate = f"{prefix}-dn0-{attempt}{suffix}"
+        if candidate not in srcs:
+            srcs.append(candidate)
+
+    logger.debug(f"Checkpoint source candidates ({len(srcs)}): {srcs}")
+    return srcs
+
+
 @contextlib.contextmanager
 def setup_execution(
     raw_output_data_prefix: str,
@@ -440,8 +502,9 @@ def setup_execution(
 
     checkpointer = None
     if checkpoint_path is not None:
-        checkpointer = SyncCheckpoint(checkpoint_dest=checkpoint_path, checkpoint_src=prev_checkpoint)
-        logger.debug(f"Checkpointer created with source {prev_checkpoint} and dest {checkpoint_path}")
+        checkpoint_srcs = _build_checkpoint_src_list(checkpoint_path, prev_checkpoint)
+        checkpointer = SyncCheckpoint(checkpoint_dest=checkpoint_path, checkpoint_src=checkpoint_srcs)
+        logger.debug(f"Checkpointer created with {len(checkpoint_srcs)} source(s) and dest {checkpoint_path}")
 
     execution_parameters = ExecutionParameters(
         execution_id=_identifier.WorkflowExecutionIdentifier(
diff --git a/flytekit/core/checkpointer.py b/flytekit/core/checkpointer.py
index d0fdf129e4..7a9aadfc3a 100644
--- a/flytekit/core/checkpointer.py
+++ b/flytekit/core/checkpointer.py
@@ -1,9 +1,12 @@
 import io
+import logging
 import tempfile
 import typing
 from abc import abstractmethod
 from pathlib import Path
 
+logger = logging.getLogger(__name__)
+
 
 class Checkpoint(object):
     """
@@ -72,14 +75,27 @@ class SyncCheckpoint(Checkpoint):
     SRC_LOCAL_FOLDER = "prev_cp"
     TMP_DST_PATH = "_dst_cp"
 
-    def __init__(self, checkpoint_dest: str, checkpoint_src: typing.Optional[str] = None):
+    def __init__(
+        self,
+        checkpoint_dest: str,
+        checkpoint_src: typing.Optional[typing.Union[str, typing.List[str]]] = None,
+    ):
         """
         Args:
-            checkpoint_src: If a previous checkpoint should exist, this path should be set to the folder that contains the checkpoint information
-            checkpoint_dest: Location where the new checkpoint should be copied to
+            checkpoint_src: One or more paths to previous checkpoint directories, tried in order.
+                Accepts a single path string or a list of path strings (most-recent-attempt first).
+                The first path that contains data wins.
+            checkpoint_dest: Location where the new checkpoint should be copied to.
         """
         self._checkpoint_dest = checkpoint_dest
-        self._checkpoint_src = checkpoint_src if checkpoint_src and checkpoint_src != "" else None
+        if checkpoint_src is None:
+            self._checkpoint_srcs: typing.List[str] = []
+        elif isinstance(checkpoint_src, str):
+            self._checkpoint_srcs = [checkpoint_src] if checkpoint_src != "" else []
+        else:
+            self._checkpoint_srcs = [s for s in checkpoint_src if s and s != ""]
+        # Keep for backwards-compat: first candidate (or None)
+        self._checkpoint_src = self._checkpoint_srcs[0] if self._checkpoint_srcs else None
         self._td = tempfile.TemporaryDirectory()
         self._prev_download_path: typing.Optional[Path] = None
 
@@ -87,13 +103,29 @@ def __del__(self):
         self._td.cleanup()
 
     def prev_exists(self) -> bool:
-        return self._checkpoint_src is not None
+        return len(self._checkpoint_srcs) > 0
 
     def restore(self, path: typing.Optional[typing.Union[Path, str]] = None) -> typing.Optional[Path]:
+        """Download a previous checkpoint, walking back through attempts until one succeeds.
+
+        Tries each candidate in ``self._checkpoint_srcs`` (most-recent first). The first
+        path that contains data is used. On success the checkpoint is also copied to
+        ``checkpoint_dest`` so the *next* attempt can find it without walking back again.
+
+        Args:
+            path: Local directory to download into. A temp directory is used when *None*.
+
+        Returns:
+            The local path where the checkpoint was restored, or *None* if no candidates exist.
+
+        Raises:
+            ValueError: If *path* is not a directory.
+            FlyteDataNotFoundException: If none of the candidates contain data.
+        """
         # We have to lazy load, until we fix the imports
         from flytekit.core.context_manager import FlyteContextManager
 
-        if self._checkpoint_src is None or self._checkpoint_src == "":
+        if not self._checkpoint_srcs:
             return None
 
         if self._prev_download_path:
@@ -109,10 +141,50 @@ def restore(self, path: typing.Optional[typing.Union[Path, str]] = None) -> typi
         if not path.is_dir():
             raise ValueError("Checkpoints can be restored to a directory only.")
 
-        FlyteContextManager.current_context().file_access.download_directory(self._checkpoint_src, str(path))
+        fa = FlyteContextManager.current_context().file_access
+        last_err: typing.Optional[Exception] = None
+
+        for idx, src in enumerate(self._checkpoint_srcs):
+            try:
+                fa.download_directory(src, str(path))
+                # Check that the download actually produced files
+                if any(path.iterdir()):
+                    logger.info(f"Checkpoint restored from candidate {idx}: {src}")
+                    self._prev_download_path = path
+                    self._auto_forward(fa, path)
+                    return self._prev_download_path
+                # Empty directory — treat as missing and try the next candidate
+                logger.debug(f"Checkpoint candidate {idx} was empty: {src}")
+            except Exception as e:
+                logger.debug(f"Checkpoint candidate {idx} failed ({src}): {e}")
+                last_err = e
+
+        # None of the candidates worked. Re-raise the last download error if we had one,
+        # otherwise fall through to the original single-source behaviour so existing
+        # callers see the same exception they always did.
+        if last_err is not None:
+            raise last_err
+
+        # All candidates were empty directories — download from the first source so the
+        # original behaviour (returning the path) is preserved.
+        fa.download_directory(self._checkpoint_srcs[0], str(path))
         self._prev_download_path = path
         return self._prev_download_path
 
+    def _auto_forward(self, fa: typing.Any, local_path: Path) -> None:
+        """Copy a successfully restored checkpoint to this attempt's dest path.
+
+        This "auto-forward" ensures that the next retry can always find a valid
+        checkpoint at attempt N's path even if N is killed before writing its own.
+        """
+        try:
+            if self._checkpoint_dest:
+                fa.upload_directory(str(local_path), self._checkpoint_dest)
+                logger.debug(f"Auto-forwarded checkpoint to {self._checkpoint_dest}")
+        except Exception:
+            # Best-effort — don't let a forwarding failure block the restore.
+            logger.warning("Failed to auto-forward checkpoint to dest", exc_info=True)
+
     def save(self, cp: typing.Union[Path, str, io.BufferedReader]):
         # We have to lazy load, until we fix the imports
         from flytekit.core.context_manager import FlyteContextManager