diff --git a/GenerateReport.py b/GenerateReport.py
index f845b48..f7d1cc3 100644
--- a/GenerateReport.py
+++ b/GenerateReport.py
@@ -37,7 +37,8 @@
     GetPyPiInfo
 )
 from utils.VersionSuggester import (
-    suggest_safe_minor_upgrade
+    suggest_safe_minor_upgrade,
+    find_latest_safe_version_for_major
 )
 from utils.VulnChecker import (
     check_cv_uv
@@ -216,6 +217,59 @@ def main() -> None:
             else:
                 instruction = generate_upgrade_instruction(pkg, suggested)
 
+        outdated_instruction = None
+        outdated_target_version = None
+
+        try:
+            cur_ver_obj = version.parse(cur_ver)
+        except InvalidVersion:
+            cur_ver_obj = None
+
+        if cur_ver_obj and all_vs:
+            available_majors = sorted({version.parse(v).major for v in all_vs})
+            if available_majors:
+                latest_major_available = available_majors[-1]
+                if cur_ver_obj.major == latest_major_available:
+                    target_major = cur_ver_obj.major
+                else:
+                    lower_majors = [m for m in available_majors if m < latest_major_available]
+                    target_major = lower_majors[-1] if lower_majors else cur_ver_obj.major
+                    if target_major < cur_ver_obj.major:
+                        target_major = cur_ver_obj.major
+
+                if (
+                    target_major in available_majors
+                    and not (target_major == cur_ver_obj.major and not newer)
+                ):
+                    try:
+                        outdated_target_version = asyncio.run(
+                            find_latest_safe_version_for_major(
+                                pkg, cur_ver, all_vs, target_major
+                            )
+                        )
+                    except Exception as e:
+                        logger.warning(
+                            f"Failed to compute outdated-oriented upgrade for {pkg}: {e}"
+                        )
+
+                if (
+                    outdated_target_version
+                    and outdated_target_version != cur_ver
+                ):
+                    try:
+                        outdated_instruction = generate_upgrade_instruction(
+                            pkg, outdated_target_version
+                        )
+                    except Exception as e:
+                        logger.warning(
+                            "Failed to generate outdated-oriented instruction for "
+                            f"{pkg}=={outdated_target_version}: {e}"
+                        )
+                        outdated_instruction = {
+                            "base_package": f"{pkg}=={outdated_target_version}",
+                            "dependencies": []
+                        }
+
         # Current version dependency JSON (only for base packages)
         if pkg.lower() in base_packages:
             current_json = generate_current_dependency_json(pkg, cur_ver, cur_ver_deps)
@@ -253,6 +307,7 @@ def main() -> None:
             'Upgrade Vulnerability Details': upgrade_vuln_details,
             'Suggested Upgrade': suggested,
             'Upgrade Instruction': instruction,
+            'Outdated-oriented Upgrade Instruction': outdated_instruction,
             'Remarks': Remarks
         })
         logger.debug(f"Custodian for {pkg}: {custodian}")
@@ -319,7 +374,7 @@ def main() -> None:
         'Dependencies for Current', 'Newer Versions', 'Dependencies for Latest',
         'Latest Version', 'Current Version Vulnerable?', 'Current Version Vulnerability Details',
         'Upgrade Version Vulnerable?', 'Upgrade Vulnerability Details',
-        'Suggested Upgrade', 'Remarks'
+        'Suggested Upgrade', 'Outdated-oriented Upgrade Instruction', 'Remarks'
     ]]
     # Overview Sheet
     total_packages = len(monthly_df)
diff --git a/utils/VersionSuggester.py b/utils/VersionSuggester.py
index 9daf308..3de740c 100644
--- a/utils/VersionSuggester.py
+++ b/utils/VersionSuggester.py
@@ -133,6 +133,82 @@ async def suggest_safe_minor_upgrade(
         return "unknown"
 
 
+async def find_latest_safe_version_for_major(
+    pkg: str,
+    current_version: str,
+    all_versions: list[str],
+    target_major: int,
+) -> str | None:
+    """Return the newest vulnerability-free version within ``target_major``.
+
+    The candidate list is restricted to the specified major version. When the
+    target major matches the current version's major, only versions greater
+    than or equal to the current version are evaluated to avoid unnecessary
+    downgrades.  The function iterates from the newest candidate backwards and
+    returns the first version confirmed to be free of known vulnerabilities.
+
+    Parameters
+    ----------
+    pkg:
+        Package name on PyPI.
+    current_version:
+        Currently installed version string.  Used to filter out downgrades
+        when ``target_major`` equals the current major release.
+    all_versions:
+        Collection of available release versions (string representation).
+    target_major:
+        Major version number that should be evaluated.
+
+    Returns
+    -------
+    str | None
+        The newest vulnerability-free version string within the selected
+        major. ``None`` if no suitable release could be found or validated.
+    """
+
+    try:
+        cur_ver = version.parse(current_version)
+    except InvalidVersion:
+        cur_ver = None
+
+    candidates: list[tuple[version.Version, str]] = []
+    for ver_str in all_versions:
+        try:
+            parsed = version.parse(ver_str)
+        except InvalidVersion:
+            continue
+
+        if parsed.major != target_major:
+            continue
+
+        if cur_ver and parsed.major == cur_ver.major and parsed < cur_ver:
+            # Skip downgrades within the same major release
+            continue
+
+        candidates.append((parsed, ver_str))
+
+    if not candidates:
+        return None
+
+    candidates.sort(reverse=True, key=lambda item: item[0])
+
+    async with aiohttp.ClientSession() as session:
+        sem = asyncio.Semaphore(5)
+        for _, ver_str in candidates:
+            try:
+                _, status, _ = await fetch_osv(session, pkg, ver_str, sem)
+            except Exception as exc:  # pragma: no cover - network safety
+                logger.warning(
+                    f"Failed to verify vulnerabilities for {pkg}=={ver_str}: {exc}"
+                )
+                continue
+
+            if status == "No":
+                return ver_str
+
+    return None
+
+
 def main():
     """
     Parses command-line arguments and suggests upgrade versions for a specified Python package.