diff --git a/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.test.ts b/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.test.ts
index fb17c34713fd8..3c98dc0e5dac5 100644
--- a/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.test.ts
+++ b/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.test.ts
@@ -5426,14 +5426,19 @@ describe("ClaudeAdapterV2 background wake turns", () => {
 
       const providerTurn = lastProviderTurn(harness.events);
       assert.notEqual(providerTurn.nativeTurnRef?.nativeId, subagentUuid);
-      const rollbackTo = (providerThreadTurns: ReadonlyArray<typeof providerTurn>) =>
+      const rollbackTo = (
+        providerThreadTurns: ReadonlyArray<typeof providerTurn>,
+        text = "Background task completed.",
+        targetTurn = providerTurn,
+      ) =>
         harness.runtime.rollbackThread({
           providerThread: harness.providerThread,
           target: {
             type: "provider_turn",
             checkpointId: CheckpointId.make("checkpoint-claude-cursor-subagent-only"),
             appRunOrdinal: 1,
-            providerTurn,
+            providerTurn: targetTurn,
+            message: { role: "user", text, attachments: [] },
           },
           providerThreadTurns,
         });
@@ -5450,6 +5455,64 @@ describe("ClaudeAdapterV2 background wake turns", () => {
       ]).pipe(Effect.flip);
       assert.instanceOf(error, ProviderAdapter.ProviderAdapterRollbackThreadError);
       assert.include(String(error.cause), "no SDK assistant message cursor");
+      const earlierCursor = "00000000-0000-4000-8000-000000000648";
+      const turnsAcrossSilent = [
+        {
+          ...providerTurn,
+          id: ProviderTurnId.make("provider-turn-claude-cursor-earlier"),
+          ordinal: providerTurn.ordinal - 1,
+          nativeTurnRef: {
+            driver: ClaudeAdapterV2.CLAUDE_PROVIDER,
+            nativeId: earlierCursor,
+            strength: "weak",
+          },
+        },
+        providerTurn,
+        {
+          ...providerTurn,
+          id: ProviderTurnId.make("provider-turn-claude-cursor-next"),
+          ordinal: providerTurn.ordinal + 1,
+        },
+      ] satisfies ReadonlyArray<typeof providerTurn>;
+      const semanticError = yield* rollbackTo(turnsAcrossSilent).pipe(Effect.flip);
+      assert.instanceOf(semanticError, ProviderAdapter.ProviderAdapterRollbackThreadError);
+      const pastSilentTurn = yield* rollbackTo(turnsAcrossSilent, "/compact");
+      assert.equal(
+        pastSilentTurn.providerThread.nativeConversationHeadRef?.nativeId,
+        earlierCursor,
+      );
+      const interruptedBeforeCompact = yield* rollbackTo(
+        [
+          {
+            ...providerTurn,
+            id: ProviderTurnId.make("provider-turn-claude-cursor-earlier"),
+            ordinal: 1,
+            nativeTurnRef: {
+              driver: ClaudeAdapterV2.CLAUDE_PROVIDER,
+              nativeId: earlierCursor,
+              strength: "weak",
+            },
+          },
+          {
+            ...providerTurn,
+            id: ProviderTurnId.make("provider-turn-claude-interrupted-before-compact"),
+            ordinal: 2,
+            status: "interrupted",
+          },
+          { ...providerTurn, ordinal: 3 },
+          {
+            ...providerTurn,
+            id: ProviderTurnId.make("provider-turn-claude-cursor-next"),
+            ordinal: 4,
+          },
+        ],
+        "/compact",
+        { ...providerTurn, ordinal: 3 },
+      ).pipe(Effect.flip);
+      assert.instanceOf(
+        interruptedBeforeCompact,
+        ProviderAdapter.ProviderAdapterRollbackThreadError,
+      );
 
       yield* harness.runtime.startTurn(
         makeClaudeTestTurnInput({
diff --git a/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.ts b/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.ts
index 496a0b2e77d0f..5f966fe05d680 100644
--- a/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.ts
+++ b/apps/server/src/orchestration-v2/Adapters/ClaudeAdapterV2.ts
@@ -1922,6 +1922,16 @@ const getNativeThreadId = Effect.fnUntraced(function* (
 
 const isSyntheticClaudeTurnId = (nativeTurnId: string): boolean => nativeTurnId.startsWith("turn:");
 
+const claudeTurnCursor = (turn: OrchestrationV2ProviderTurn): string | null => {
+  const ref = turn.nativeTurnRef;
+  return ref !== null &&
+    ref.driver === CLAUDE_PROVIDER &&
+    ref.nativeId !== null &&
+    !isSyntheticClaudeTurnId(ref.nativeId)
+    ? ref.nativeId
+    : null;
+};
+
 const isTerminalProviderTurn = (turn: OrchestrationV2ProviderTurn): boolean =>
   turn.status === "completed" ||
   turn.status === "interrupted" ||
@@ -2008,14 +2018,9 @@ const resolveClaudeRollbackResumeSessionAt = Effect.fn(
         });
       }
 
-      const nativeTurnRef = target.providerTurn.nativeTurnRef;
-      if (
-        nativeTurnRef !== null &&
-        nativeTurnRef.driver === CLAUDE_PROVIDER &&
-        nativeTurnRef.nativeId !== null &&
-        !isSyntheticClaudeTurnId(nativeTurnRef.nativeId)
-      ) {
-        return nativeTurnRef.nativeId;
+      const cursor = claudeTurnCursor(target.providerTurn);
+      if (cursor !== null) {
+        return cursor;
       }
 
       const providerTurnsAfterTarget = input.providerThreadTurns.filter(
@@ -2025,6 +2030,18 @@ const resolveClaudeRollbackResumeSessionAt = Effect.fn(
         return null;
       }
 
+      // Only compaction can be omitted without dropping a retained user prompt.
+      if (target.message !== undefined && isCompactionCommandMessage(target.message)) {
+        const earlierTurn = input.providerThreadTurns
+          .filter((turn) => turn.ordinal < target.providerTurn.ordinal)
+          .toSorted((left, right) => left.ordinal - right.ordinal)
+          .at(-1);
+        const earlierCursor = earlierTurn === undefined ? null : claudeTurnCursor(earlierTurn);
+        if (earlierCursor != null) {
+          return earlierCursor;
+        }
+      }
+
       return yield* new ProviderAdapter.ProviderAdapterRollbackThreadError({
         driver: CLAUDE_PROVIDER,
         providerThreadId: input.providerThread.id,
diff --git a/apps/server/src/orchestration-v2/CheckpointRollbackService.ts b/apps/server/src/orchestration-v2/CheckpointRollbackService.ts
index 385de626cfdf8..120efef2eaeec 100644
--- a/apps/server/src/orchestration-v2/CheckpointRollbackService.ts
+++ b/apps/server/src/orchestration-v2/CheckpointRollbackService.ts
@@ -183,7 +183,11 @@ export const layer: Layer.Layer<
               const targetTurn =
                 latestProviderTurnForAttempt(context.providerTurns, targetAttempt?.id) ??
                 context.providerTurns.find((turn) => turn.id === targetAttempt?.providerTurnId);
-              if (targetTurn === undefined || targetTurn.providerThreadId !== providerThread.id) {
+              if (
+                targetAttempt === undefined ||
+                targetTurn === undefined ||
+                targetTurn.providerThreadId !== providerThread.id
+              ) {
                 return yield* new CheckpointRollbackExecutionError({
                   reason: "provider-turn-unavailable",
                   threadId: input.threadId,
@@ -191,11 +195,21 @@ export const layer: Layer.Layer<
                   checkpointId: input.checkpointId,
                 });
               }
+              const { attempt } = yield* projections.getProviderControlContext(input.threadId, {
+                providerThreadId: providerThread.id,
+                providerTurnId: targetTurn.id,
+                attemptId: targetAttempt.id,
+              });
+              const message =
+                attempt === undefined
+                  ? undefined
+                  : yield* projections.getRunMessage(input.threadId, attempt.runId);
               return {
                 type: "provider_turn" as const,
                 checkpointId: checkpoint.id,
                 appRunOrdinal: targetOrdinal,
                 providerTurn: targetTurn,
+                ...(message === undefined ? {} : { message }),
               };
             });
 
diff --git a/packages/provider-core/src/server/ProviderAdapter.ts b/packages/provider-core/src/server/ProviderAdapter.ts
index e168512736c7c..adcf5ac0b11e7 100644
--- a/packages/provider-core/src/server/ProviderAdapter.ts
+++ b/packages/provider-core/src/server/ProviderAdapter.ts
@@ -475,6 +475,7 @@ export type ProviderAdapterV2RollbackTarget =
       readonly checkpointId: CheckpointId;
       readonly appRunOrdinal: number;
       readonly providerTurn: OrchestrationV2ProviderTurn;
+      readonly message?: Pick<OrchestrationV2ConversationMessage, "role" | "text" | "attachments">;
     };
 
 export interface ProviderAdapterV2RollbackThreadInput {