diff --git a/packages/SystemUI/proguard_common.flags b/packages/SystemUI/proguard_common.flags
index be1e655..445bdc2 100644
--- a/packages/SystemUI/proguard_common.flags
+++ b/packages/SystemUI/proguard_common.flags
@@ -2,45 +2,17 @@
 
 # Needed to ensure callback field references are kept in their respective
 # owning classes when the downstream callback registrars only store weak refs.
-# TODO(b/264686688): Handle these cases with more targeted annotations.
--keepclassmembers,allowaccessmodification class com.android.systemui.**, com.android.keyguard.** {
-  private com.android.keyguard.KeyguardUpdateMonitorCallback *;
-  private com.android.systemui.privacy.PrivacyConfig$Callback *;
-  private com.android.systemui.privacy.PrivacyItemController$Callback *;
-  private com.android.systemui.settings.UserTracker$Callback *;
-  private com.android.systemui.statusbar.phone.StatusBarWindowCallback *;
-  private com.android.systemui.util.service.Observer$Callback *;
-  private com.android.systemui.util.service.ObservableServiceConnection$Callback *;
-}
-# Note that these rules are temporary companions to the above rules, required
-# for cases like Kotlin where fields with anonymous types use the anonymous type
-# rather than the supertype.
--if class * extends com.android.keyguard.KeyguardUpdateMonitorCallback
--keepclassmembers,allowaccessmodification class com.android.systemui.**, com.android.keyguard.** {
+# Note that we restrict this to SysUISingleton classes, as other registering
+# classes should either *always* unregister or *never* register from their
+# constructor. We also keep callback class names for easier debugging.
+-keepnames @com.android.systemui.util.annotations.WeaklyReferencedCallback class *
+-keepnames class * extends @com.android.systemui.util.annotations.WeaklyReferencedCallback **
+-if @com.android.systemui.util.annotations.WeaklyReferencedCallback class *
+-keepclassmembers,allowaccessmodification @com.android.systemui.dagger.SysUISingleton class * {
   <1> *;
 }
--if class * extends com.android.systemui.privacy.PrivacyConfig$Callback
--keepclassmembers,allowaccessmodification class com.android.systemui.**, com.android.keyguard.** {
-  <1> *;
-}
--if class * extends com.android.systemui.privacy.PrivacyItemController$Callback
--keepclassmembers,allowaccessmodification class com.android.systemui.**, com.android.keyguard.** {
-  <1> *;
-}
--if class * extends com.android.systemui.settings.UserTracker$Callback
--keepclassmembers,allowaccessmodification class com.android.systemui.**, com.android.keyguard.** {
-  <1> *;
-}
--if class * extends com.android.systemui.statusbar.phone.StatusBarWindowCallback
--keepclassmembers,allowaccessmodification class com.android.systemui.**, com.android.keyguard.** {
-  <1> *;
-}
--if class * extends com.android.systemui.util.service.Observer$Callback
--keepclassmembers,allowaccessmodification class com.android.systemui.**, com.android.keyguard.** {
-  <1> *;
-}
--if class * extends com.android.systemui.util.service.ObservableServiceConnection$Callback
--keepclassmembers,allowaccessmodification class com.android.systemui.**, com.android.keyguard.** {
+-if class * extends @com.android.systemui.util.annotations.WeaklyReferencedCallback **
+-keepclassmembers,allowaccessmodification @com.android.systemui.dagger.SysUISingleton class * {
   <1> *;
 }
 
diff --git a/packages/SystemUI/src/com/android/keyguard/KeyguardUpdateMonitorCallback.java b/packages/SystemUI/src/com/android/keyguard/KeyguardUpdateMonitorCallback.java
index 7b59632..2476067 100644
--- a/packages/SystemUI/src/com/android/keyguard/KeyguardUpdateMonitorCallback.java
+++ b/packages/SystemUI/src/com/android/keyguard/KeyguardUpdateMonitorCallback.java
@@ -25,12 +25,14 @@
 import com.android.settingslib.fuelgauge.BatteryStatus;
 import com.android.systemui.plugins.WeatherData;
 import com.android.systemui.statusbar.KeyguardIndicationController;
+import com.android.systemui.util.annotations.WeaklyReferencedCallback;
 
 import java.util.TimeZone;
 
 /**
  * Callback for general information relevant to lock screen.
  */
+@WeaklyReferencedCallback
 public class KeyguardUpdateMonitorCallback {
 
     /**
diff --git a/packages/SystemUI/src/com/android/systemui/media/controls/pipeline/MediaDataFilter.kt b/packages/SystemUI/src/com/android/systemui/media/controls/pipeline/MediaDataFilter.kt
index a1291a4..724241d 100644
--- a/packages/SystemUI/src/com/android/systemui/media/controls/pipeline/MediaDataFilter.kt
+++ b/packages/SystemUI/src/com/android/systemui/media/controls/pipeline/MediaDataFilter.kt
@@ -19,6 +19,7 @@
 import android.content.Context
 import android.os.SystemProperties
 import android.util.Log
+import com.android.internal.annotations.KeepForWeakReference
 import com.android.internal.annotations.VisibleForTesting
 import com.android.systemui.broadcast.BroadcastSender
 import com.android.systemui.dagger.qualifiers.Main
@@ -82,6 +83,8 @@
     private var smartspaceMediaData: SmartspaceMediaData = EMPTY_SMARTSPACE_MEDIA_DATA
     private var reactivatedKey: String? = null
 
+    // Ensure the field (and associated reference) isn't removed during optimization.
+    @KeepForWeakReference
     private val userTrackerCallback =
         object : UserTracker.Callback {
             override fun onUserChanged(newUser: Int, userContext: Context) {
diff --git a/packages/SystemUI/src/com/android/systemui/privacy/PrivacyConfig.kt b/packages/SystemUI/src/com/android/systemui/privacy/PrivacyConfig.kt
index d949a2a..67d390d 100644
--- a/packages/SystemUI/src/com/android/systemui/privacy/PrivacyConfig.kt
+++ b/packages/SystemUI/src/com/android/systemui/privacy/PrivacyConfig.kt
@@ -25,6 +25,7 @@
 import com.android.systemui.dump.DumpManager
 import com.android.systemui.util.DeviceConfigProxy
 import com.android.systemui.util.asIndenting
+import com.android.systemui.util.annotations.WeaklyReferencedCallback
 import com.android.systemui.util.concurrency.DelayableExecutor
 import com.android.systemui.util.withIncreasedIndent
 import java.io.PrintWriter
@@ -144,6 +145,7 @@
         ipw.flush()
     }
 
+    @WeaklyReferencedCallback
     interface Callback {
         fun onFlagMicCameraChanged(flag: Boolean) {}
 
diff --git a/packages/SystemUI/src/com/android/systemui/settings/UserTracker.kt b/packages/SystemUI/src/com/android/systemui/settings/UserTracker.kt
index bd592c9..cf1fbe3 100644
--- a/packages/SystemUI/src/com/android/systemui/settings/UserTracker.kt
+++ b/packages/SystemUI/src/com/android/systemui/settings/UserTracker.kt
@@ -16,6 +16,8 @@
 
 package com.android.systemui.settings
 
+import com.android.systemui.util.annotations.WeaklyReferencedCallback
+
 import android.content.Context
 import android.content.pm.UserInfo
 import android.os.UserHandle
@@ -64,6 +66,7 @@
     /**
      * Callback for notifying of changes.
      */
+    @WeaklyReferencedCallback
     interface Callback {
 
         /**
diff --git a/packages/SystemUI/src/com/android/systemui/statusbar/phone/StatusBarWindowCallback.java b/packages/SystemUI/src/com/android/systemui/statusbar/phone/StatusBarWindowCallback.java
index 6dc8065..da91d6a 100644
--- a/packages/SystemUI/src/com/android/systemui/statusbar/phone/StatusBarWindowCallback.java
+++ b/packages/SystemUI/src/com/android/systemui/statusbar/phone/StatusBarWindowCallback.java
@@ -15,6 +15,9 @@
  */
 package com.android.systemui.statusbar.phone;
 
+import com.android.systemui.util.annotations.WeaklyReferencedCallback;
+
+@WeaklyReferencedCallback
 public interface StatusBarWindowCallback {
     /**
      * Invoked when the internal state of NotificationShadeWindowControllerImpl changes.
diff --git a/packages/SystemUI/src/com/android/systemui/util/annotations/WeaklyReferencedCallback.java b/packages/SystemUI/src/com/android/systemui/util/annotations/WeaklyReferencedCallback.java
new file mode 100644
index 0000000..855bba6
--- /dev/null
+++ b/packages/SystemUI/src/com/android/systemui/util/annotations/WeaklyReferencedCallback.java
@@ -0,0 +1,35 @@
+/*
+ * Copyright (C) 2023 The Android Open Source Project
+ *
+ * Licensed under the Apache License, Version 2.0 (the "License");
+ * you may not use this file except in compliance with the License.
+ * You may obtain a copy of the License at
+ *
+ *      http://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing, software
+ * distributed under the License is distributed on an "AS IS" BASIS,
+ * WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+ * See the License for the specific language governing permissions and
+ * limitations under the License.
+ */
+
+package com.android.systemui.util.annotations;
+
+import static java.lang.annotation.ElementType.TYPE;
+
+import java.lang.annotation.Retention;
+import java.lang.annotation.RetentionPolicy;
+import java.lang.annotation.Target;
+
+
+/**
+ * Descriptive annotation for clearly tagging callback types that are weakly
+ * referenced during registration.
+ *
+ * This is useful in providing hints to Proguard about certain fields that
+ * should be kept to preserve strong references.
+ */
+@Retention(RetentionPolicy.CLASS)
+@Target({TYPE})
+public @interface WeaklyReferencedCallback {}
diff --git a/packages/SystemUI/src/com/android/systemui/util/service/ObservableServiceConnection.java b/packages/SystemUI/src/com/android/systemui/util/service/ObservableServiceConnection.java
index 968dcc9..df5162a 100644
--- a/packages/SystemUI/src/com/android/systemui/util/service/ObservableServiceConnection.java
+++ b/packages/SystemUI/src/com/android/systemui/util/service/ObservableServiceConnection.java
@@ -26,6 +26,7 @@
 
 import com.android.systemui.dagger.qualifiers.Main;
 import com.android.systemui.settings.UserTracker;
+import com.android.systemui.util.annotations.WeaklyReferencedCallback;
 
 import java.lang.annotation.Retention;
 import java.lang.annotation.RetentionPolicy;
@@ -64,6 +65,7 @@
      * An interface for listening to the connection status.
      * @param <T> The wrapper type.
      */
+    @WeaklyReferencedCallback
     public interface Callback<T> {
         /**
          * Invoked when the service has been successfully connected to.
diff --git a/packages/SystemUI/src/com/android/systemui/util/service/Observer.java b/packages/SystemUI/src/com/android/systemui/util/service/Observer.java
index 7687432..425336d 100644
--- a/packages/SystemUI/src/com/android/systemui/util/service/Observer.java
+++ b/packages/SystemUI/src/com/android/systemui/util/service/Observer.java
@@ -16,6 +16,8 @@
 
 package com.android.systemui.util.service;
 
+import com.android.systemui.util.annotations.WeaklyReferencedCallback;
+
 /**
  * The {@link Observer} interface specifies an entity which listeners
  * can be informed of changes to the source, which will require updating. Note that this deals
@@ -25,6 +27,7 @@
     /**
      * Callback for receiving updates from the {@link Observer}.
      */
+    @WeaklyReferencedCallback
     interface Callback {
         /**
          * Invoked when the source has changed.