diff --git a/app/src/main/java/org/thoughtcrime/securesms/conversation/v2/utilities/ThumbnailView.kt b/app/src/main/java/org/thoughtcrime/securesms/conversation/v2/utilities/ThumbnailView.kt
index 83932b2ce4..b7103b9c23 100644
--- a/app/src/main/java/org/thoughtcrime/securesms/conversation/v2/utilities/ThumbnailView.kt
+++ b/app/src/main/java/org/thoughtcrime/securesms/conversation/v2/utilities/ThumbnailView.kt
@@ -9,6 +9,7 @@ import android.util.AttributeSet
 import android.util.TypedValue
 import android.view.View
 import android.view.ViewOutlineProvider
+import android.view.ViewTreeObserver
 import android.widget.FrameLayout
 import androidx.core.view.isVisible
 import com.bumptech.glide.load.engine.DiskCacheStrategy
@@ -27,7 +28,10 @@ import org.thoughtcrime.securesms.components.GlideDrawableListeningTarget
 import org.thoughtcrime.securesms.mms.DecryptableStreamUriLoader.DecryptableUri
 import com.bumptech.glide.RequestBuilder
 import com.bumptech.glide.RequestManager
+import org.session.libsignal.utilities.Log
 import org.thoughtcrime.securesms.mms.Slide
+import org.thoughtcrime.securesms.ui.afterMeasured
+import java.lang.Float.min
 
 open class ThumbnailView @JvmOverloads constructor(
     context: Context,
@@ -114,8 +118,23 @@ open class ThumbnailView @JvmOverloads constructor(
         isPreview: Boolean, naturalWidth: Int,
         naturalHeight: Int
     ): ListenableFuture<Boolean> {
-        binding.playOverlay.isVisible = (slide.thumbnailUri != null && slide.hasPlayOverlay() &&
-            (slide.transferState == AttachmentTransferProgress.TRANSFER_PROGRESS_DONE || isPreview))
+        val showPlayOverlay = (slide.thumbnailUri != null && slide.hasPlayOverlay() &&
+                (slide.transferState == AttachmentTransferProgress.TRANSFER_PROGRESS_DONE || isPreview))
+        if(showPlayOverlay) {
+            binding.playOverlay.isVisible = true
+            // The views are poorly constructed at the moment and there is no good way to know
+            // if this is used in the main conversation or in the tiny quote window of a reply...
+            // But when the view is too small the 'play' icon does not scale,
+            // so we can do it based on measured sizes here
+            binding.playOverlay.afterMeasured {
+                // max size if 60% of the width
+                val ratio = min((binding.root.width * 0.6f) / binding.playOverlay.width, 1f)
+                binding.playOverlay.scaleX = ratio
+                binding.playOverlay.scaleY = ratio
+            }
+        } else {
+            binding.playOverlay.isVisible = false
+        }
 
         if (equals(this.slide, slide)) {
             // don't re-load slide
diff --git a/app/src/main/java/org/thoughtcrime/securesms/ui/Util.kt b/app/src/main/java/org/thoughtcrime/securesms/ui/Util.kt
index 22eb4bf860..3dec8d5a2e 100644
--- a/app/src/main/java/org/thoughtcrime/securesms/ui/Util.kt
+++ b/app/src/main/java/org/thoughtcrime/securesms/ui/Util.kt
@@ -3,6 +3,8 @@ package org.thoughtcrime.securesms.ui
 import android.app.Activity
 import android.content.Context
 import android.content.ContextWrapper
+import android.view.View
+import android.view.ViewTreeObserver
 import androidx.compose.runtime.Composable
 import androidx.compose.ui.platform.ComposeView
 import androidx.fragment.app.Fragment
@@ -58,3 +60,14 @@ fun Context.findActivity(): Activity {
     }
     throw IllegalStateException("Permissions should be called in the context of an Activity")
 }
+
+inline fun <T : View> T.afterMeasured(crossinline block: T.() -> Unit) {
+    viewTreeObserver.addOnGlobalLayoutListener(object : ViewTreeObserver.OnGlobalLayoutListener {
+        override fun onGlobalLayout() {
+            if (measuredWidth > 0 && measuredHeight > 0) {
+                viewTreeObserver.removeOnGlobalLayoutListener(this)
+                block()
+            }
+        }
+    })
+}
diff --git a/app/src/main/res/drawable/image_loading_background.xml b/app/src/main/res/drawable/image_loading_background.xml
index d2e3dfbfa7..04c4a8a2a0 100644
--- a/app/src/main/res/drawable/image_loading_background.xml
+++ b/app/src/main/res/drawable/image_loading_background.xml
@@ -5,6 +5,4 @@
 
     <solid android:color="?backgroundSecondary" />
 
-    <corners android:radius="?dialogCornerRadius" />
-
 </shape>
\ No newline at end of file