diff --git a/app/src/main/java/org/thoughtcrime/securesms/mms/PushMediaConstraints.java b/app/src/main/java/org/thoughtcrime/securesms/mms/PushMediaConstraints.java
index 1b5b1717b5..1a40253672 100644
--- a/app/src/main/java/org/thoughtcrime/securesms/mms/PushMediaConstraints.java
+++ b/app/src/main/java/org/thoughtcrime/securesms/mms/PushMediaConstraints.java
@@ -6,13 +6,15 @@ import androidx.annotation.IntRange;
 import androidx.annotation.NonNull;
 import androidx.annotation.Nullable;
 
+import org.signal.core.util.Util;
 import org.thoughtcrime.securesms.dependencies.AppDependencies;
 import org.thoughtcrime.securesms.keyvalue.SignalStore;
-import org.thoughtcrime.securesms.util.RemoteConfig;
 import org.thoughtcrime.securesms.util.LocaleRemoteConfig;
-import org.signal.core.util.Util;
+import org.thoughtcrime.securesms.util.RemoteConfig;
 import org.thoughtcrime.securesms.video.TranscodingPreset;
 import org.thoughtcrime.securesms.video.videoconverter.utils.DeviceCapabilities;
+import org.whispersystems.signalservice.api.crypto.AttachmentCipherStreamUtil;
+import org.whispersystems.signalservice.internal.crypto.PaddingInputStream;
 
 import java.util.Arrays;
 
@@ -65,7 +67,10 @@ public class PushMediaConstraints extends MediaConstraints {
 
   @Override
   public long getCompressedVideoMaxSize(Context context) {
-    return getMaxAttachmentSize();
+    long maxCipherTextSize = RemoteConfig.videoTranscodeTargetSizeBytes();
+    long maxPaddedSize     = AttachmentCipherStreamUtil.getPlaintextLength(maxCipherTextSize);
+
+    return Math.min(PaddingInputStream.getMaxUnpaddedSize(maxPaddedSize), getMaxAttachmentSize());
   }
 
   @Override
diff --git a/app/src/main/java/org/thoughtcrime/securesms/util/RemoteConfig.kt b/app/src/main/java/org/thoughtcrime/securesms/util/RemoteConfig.kt
index 8b4adddb64..abe24258a4 100644
--- a/app/src/main/java/org/thoughtcrime/securesms/util/RemoteConfig.kt
+++ b/app/src/main/java/org/thoughtcrime/securesms/util/RemoteConfig.kt
@@ -929,6 +929,15 @@ object RemoteConfig {
     hotSwappable = true
   )
 
+  /** Maximum size a video transcode should target in bytes  */
+  @JvmStatic
+  @get:JvmName("videoTranscodeTargetSizeBytes")
+  val videoTranscodeTargetSizeBytes: Long by remoteLong(
+    key = "global.videoAttachments.transcodeTargetBytes",
+    defaultValue = 100.mebiBytes.inWholeBytes,
+    hotSwappable = true
+  )
+
   /** Maximum input size when opening a video to send in bytes  */
   @JvmStatic
   @get:JvmName("maxSourceTranscodeVideoSizeBytes")