diff --git a/libs/WindowManager/Shell/src/com/android/wm/shell/pip/PipTransition.java b/libs/WindowManager/Shell/src/com/android/wm/shell/pip/PipTransition.java
index e5a755c35add6..48df28ee4cdea 100644
--- a/libs/WindowManager/Shell/src/com/android/wm/shell/pip/PipTransition.java
+++ b/libs/WindowManager/Shell/src/com/android/wm/shell/pip/PipTransition.java
@@ -89,6 +89,8 @@ public class PipTransition extends PipTransitionController {
     private final Rect mExitDestinationBounds = new Rect();
     @Nullable
     private IBinder mExitTransition;
+    private IBinder mRequestedEnterTransition;
+    private WindowContainerToken mRequestedEnterTask;
     /** The Task window that is currently in PIP windowing mode. */
     @Nullable
     private WindowContainerToken mCurrentPipTaskToken;
@@ -201,6 +203,9 @@ public class PipTransition extends PipTransitionController {
             }
             mCurrentPipTaskToken = null;
             return true;
+        } else if (transition == mRequestedEnterTransition) {
+            mRequestedEnterTransition = null;
+            mRequestedEnterTask = null;
         }
 
         // The previous PIP Task is no longer in PIP, but this is not an exit transition (This can
@@ -243,6 +248,8 @@ public class PipTransition extends PipTransitionController {
         if (request.getType() == TRANSIT_PIP) {
             WindowContainerTransaction wct = new WindowContainerTransaction();
             if (mOneShotAnimationType == ANIM_TYPE_ALPHA) {
+                mRequestedEnterTransition = transition;
+                mRequestedEnterTask = request.getTriggerTask().token;
                 wct.setActivityWindowingMode(request.getTriggerTask().token,
                         WINDOWING_MODE_UNDEFINED);
                 final Rect destinationBounds = mPipBoundsAlgorithm.getEntryDestinationBounds();
@@ -254,6 +261,23 @@ public class PipTransition extends PipTransitionController {
         }
     }
 
+    @Override
+    public boolean handleRotateDisplay(int startRotation, int endRotation,
+            WindowContainerTransaction wct) {
+        if (mRequestedEnterTransition != null && mOneShotAnimationType == ANIM_TYPE_ALPHA) {
+            // A fade-in was requested but not-yet started. In this case, just recalculate the
+            // initial state under the new rotation.
+            int rotationDelta = deltaRotation(startRotation, endRotation);
+            if (rotationDelta != Surface.ROTATION_0) {
+                mPipBoundsState.getDisplayLayout().rotateTo(mContext.getResources(), endRotation);
+                final Rect destinationBounds = mPipBoundsAlgorithm.getEntryDestinationBounds();
+                wct.setBounds(mRequestedEnterTask, destinationBounds);
+                return true;
+            }
+        }
+        return false;
+    }
+
     @Override
     public void onTransitionMerged(@NonNull IBinder transition) {
         if (transition != mExitTransition) {
diff --git a/libs/WindowManager/Shell/src/com/android/wm/shell/pip/PipTransitionController.java b/libs/WindowManager/Shell/src/com/android/wm/shell/pip/PipTransitionController.java
index 02e713d2eaa36..24993c621e3c1 100644
--- a/libs/WindowManager/Shell/src/com/android/wm/shell/pip/PipTransitionController.java
+++ b/libs/WindowManager/Shell/src/com/android/wm/shell/pip/PipTransitionController.java
@@ -195,6 +195,17 @@ public abstract class PipTransitionController implements Transitions.TransitionH
                 mPipBoundsAlgorithm);
     }
 
+    /**
+     * Called when the display is going to rotate.
+     *
+     * @return {@code true} if it was handled, otherwise the existing pip logic
+     *                      will deal with rotation.
+     */
+    public boolean handleRotateDisplay(int startRotation, int endRotation,
+            WindowContainerTransaction wct) {
+        return false;
+    }
+
     /**
      * Callback interface for PiP transitions (both from and to PiP mode)
      */
diff --git a/libs/WindowManager/Shell/src/com/android/wm/shell/pip/phone/PipController.java b/libs/WindowManager/Shell/src/com/android/wm/shell/pip/phone/PipController.java
index e86ebaaabbfe3..ba522c072f11f 100644
--- a/libs/WindowManager/Shell/src/com/android/wm/shell/pip/phone/PipController.java
+++ b/libs/WindowManager/Shell/src/com/android/wm/shell/pip/phone/PipController.java
@@ -143,6 +143,9 @@ public class PipController implements PipTransitionController.PipTransitionCallb
      */
     private final DisplayChangeController.OnDisplayChangingListener mRotationController = (
             int displayId, int fromRotation, int toRotation, WindowContainerTransaction t) -> {
+        if (mPipTransitionController.handleRotateDisplay(fromRotation, toRotation, t)) {
+            return;
+        }
         if (mPipBoundsState.getDisplayLayout().rotation() == toRotation) {
             // The same rotation may have been set by auto PiP-able or fixed rotation. So notify
             // the change with fromRotation=false to apply the rotated destination bounds from
diff --git a/services/core/java/com/android/server/wm/Transition.java b/services/core/java/com/android/server/wm/Transition.java
index 21ca4bb6038bf..557ca4c978388 100644
--- a/services/core/java/com/android/server/wm/Transition.java
+++ b/services/core/java/com/android/server/wm/Transition.java
@@ -520,7 +520,6 @@ class Transition extends Binder implements BLASTSyncEngine.TransactionReadyListe
                     // Legacy dispatch relies on this (for now).
                     ar.mEnteringAnimation = visibleAtTransitionEnd;
                 }
-                mController.dispatchLegacyAppTransitionFinished(ar);
             }
             final WallpaperWindowToken wt = mParticipants.valueAt(i).asWallpaperToken();
             if (wt != null) {
@@ -532,6 +531,15 @@ class Transition extends Binder implements BLASTSyncEngine.TransactionReadyListe
                 }
             }
         }
+        // dispatch legacy callback in a different loop. This is because multiple legacy handlers
+        // (fixed-rotation/displaycontent) make global changes, so we want to ensure that we've
+        // processed all the participants first (in particular, we want to trigger pip-enter first)
+        for (int i = 0; i < mParticipants.size(); ++i) {
+            final ActivityRecord ar = mParticipants.valueAt(i).asActivityRecord();
+            if (ar != null) {
+                mController.dispatchLegacyAppTransitionFinished(ar);
+            }
+        }
         if (activitiesWentInvisible) {
             // Always schedule stop processing when transition finishes because activities don't
             // stop while they are in a transition thus their stop could still be pending.