diff --git a/CHANGELOG.md b/CHANGELOG.md
index 29bd5fee..40642f2d 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -1,6 +1,18 @@
 # Changelog
 
-## Unreleased
+## v1.4.248 (2025-07-16)
+
+### PR [#1616](https://github.com/danielmiessler/Fabric/pull/1616) by [ksylvan](https://github.com/ksylvan): Preserve PR Numbers During Version Cache Merges
+
+- Feat: enhance changelog to correctly associate PR numbers with version tags
+- Fix: improve PR number parsing with proper error handling
+- Collect all PR numbers for commits between version tags
+- Associate aggregated PR numbers with each version entry
+- Update cached versions with newly found PR numbers
+
+### Direct commits
+
+- Docs: reorganize v1.4.247 changelog to attribute changes to PR #1613
 
 ## v1.4.247 (2025-07-15)
 
diff --git a/cmd/generate_changelog/changelog.db b/cmd/generate_changelog/changelog.db
index 8bba9fd1..4dc0baec 100644
Binary files a/cmd/generate_changelog/changelog.db and b/cmd/generate_changelog/changelog.db differ
diff --git a/cmd/generate_changelog/internal/changelog/generator.go b/cmd/generate_changelog/internal/changelog/generator.go
index 75a6a932..c6e3ba2e 100644
--- a/cmd/generate_changelog/internal/changelog/generator.go
+++ b/cmd/generate_changelog/internal/changelog/generator.go
@@ -210,8 +210,23 @@ func (g *Generator) fetchPRs() error {
 		lastSync, _ = g.cache.GetLastPRSync()
 	}
 
+	// Check if we need to sync for missing PRs
+	missingPRs := false
+	for _, version := range g.versions {
+		for _, prNum := range version.PRNumbers {
+			if _, exists := g.prs[prNum]; !exists {
+				missingPRs = true
+				break
+			}
+		}
+		if missingPRs {
+			break
+		}
+	}
+
 	// If we have never synced or it's been more than 24 hours, do a full sync
-	needsSync := lastSync.IsZero() || time.Since(lastSync) > 24*time.Hour || g.cfg.ForcePRSync
+	// Also sync if we have versions with PR numbers that aren't cached
+	needsSync := lastSync.IsZero() || time.Since(lastSync) > 24*time.Hour || g.cfg.ForcePRSync || missingPRs
 
 	if !needsSync {
 		fmt.Fprintf(os.Stderr, "Using cached PR data (last sync: %s)\n", lastSync.Format("2006-01-02 15:04:05"))