diff --git a/src/app/baseball/actions/insights.ts b/src/app/baseball/actions/insights.ts
index c977c06d2..b96093347 100644
--- a/src/app/baseball/actions/insights.ts
+++ b/src/app/baseball/actions/insights.ts
@@ -300,7 +300,10 @@ function analyzePlayer(
   if (totalHits >= 50 && totalHits % 25 === 0) {
     insights.push({
       player_id: playerId,
-      insight_type: 'development_milestone',
+      // Distinct from the HR milestone so both survive reconciliation, which
+      // keys insights by `${playerId}::${insight_type}`. A player crossing both
+      // a hit and an HR milestone in one run now persists two independent rows.
+      insight_type: 'milestone_hits',
       priority: 'low',
       title: `${playerName} reached ${totalHits} hits!`,
       description: `Career milestone: ${totalHits} hits in ${aggregates?.total_sessions || 0} sessions.`,
@@ -316,7 +319,9 @@ function analyzePlayer(
   if (totalHR >= 10 && totalHR % 5 === 0) {
     insights.push({
       player_id: playerId,
-      insight_type: 'development_milestone',
+      // Distinct from the hits milestone (see above) so the HR milestone is
+      // reconciled and refreshed independently rather than overwriting it.
+      insight_type: 'milestone_hr',
       priority: 'low',
       title: `${playerName} hit ${totalHR} home runs!`,
       description: `Power milestone achieved.`,
diff --git a/src/lib/types/index.ts b/src/lib/types/index.ts
index 2836a8140..71abc4261 100644
--- a/src/lib/types/index.ts
+++ b/src/lib/types/index.ts
@@ -108,6 +108,10 @@ export type BaseballInsightType =
   | 'breakout_candidate'
   | 'position_opportunity'
   | 'development_milestone'
+  // Milestone-kind-specific types so a player crossing both a hit and an HR
+  // milestone in one run persists both (reconcile keys by playerId::insight_type).
+  | 'milestone_hits'
+  | 'milestone_hr'
   | 'comparison_alert'
   // Additional types for AI insights engine
   | 'decline'