diff --git a/app/src/main/java/chat/rocket/android/chatroom/presentation/ChatRoomPresenter.kt b/app/src/main/java/chat/rocket/android/chatroom/presentation/ChatRoomPresenter.kt
index 9923afe1be..66bff22a26 100644
--- a/app/src/main/java/chat/rocket/android/chatroom/presentation/ChatRoomPresenter.kt
+++ b/app/src/main/java/chat/rocket/android/chatroom/presentation/ChatRoomPresenter.kt
@@ -89,6 +89,7 @@ import kotlinx.coroutines.launch
 import kotlinx.coroutines.withContext
 import org.threeten.bp.Instant
 import timber.log.Timber
+import java.io.InvalidObjectException
 import java.util.*
 import javax.inject.Inject
 
@@ -475,7 +476,7 @@ class ChatRoomPresenter @Inject constructor(
                         view.showInvalidFileMessage()
                     } else {
                         val byteArray =
-                            bitmap.getByteArray(mimeType, 100, settings.uploadMaxFileSize())
+                            bitmap.getByteArray(mimeType, 60, settings.uploadMaxFileSize())
                         retryIO("uploadFile($roomId, $fileName, $mimeType") {
                             client.uploadFile(
                                 roomId,
@@ -495,6 +496,7 @@ class ChatRoomPresenter @Inject constructor(
                 Timber.d(ex, "Error uploading image")
                 when (ex) {
                     is RocketChatException -> view.showMessage(ex)
+                    is InvalidObjectException -> view.showInvalidFileSize(bitmap.getByteCount(), settings.uploadMaxFileSize())
                     else -> view.showGenericErrorMessage()
                 }
             } finally {
diff --git a/util/src/main/java/chat/rocket/android/util/extension/Image.kt b/util/src/main/java/chat/rocket/android/util/extension/Image.kt
index 5d2fca6cd8..516dfc8d25 100644
--- a/util/src/main/java/chat/rocket/android/util/extension/Image.kt
+++ b/util/src/main/java/chat/rocket/android/util/extension/Image.kt
@@ -8,11 +8,7 @@ import androidx.fragment.app.Fragment
 import androidx.fragment.app.FragmentActivity
 import kotlinx.coroutines.Dispatchers
 import kotlinx.coroutines.withContext
-import java.io.ByteArrayInputStream
-import java.io.ByteArrayOutputStream
-import java.io.InputStream
-import java.io.IOException
-import java.io.File
+import java.io.*
 import java.text.SimpleDateFormat
 import java.util.*
 
@@ -37,13 +33,14 @@ suspend fun Bitmap.compressImageAndGetInputStream(mimeType: String): InputStream
     return inputStream
 }
 
+
 /**
  * Returns a [ByteArray] of a [Bitmap].
  *
  * @param mimeType The MIME type of the [Bitmap].
  * @param quality The quality of the [Bitmap] for the resulting [ByteArray].
  * @param maxFileSizeAllowed The max file size allowed by the server. Note: The [quality] will be
- * decreased minus 10 until the [ByteArray] size fits the [maxFileSizeAllowed] value.
+ * decreased minus 20 until the [ByteArray] size fits the [maxFileSizeAllowed] value.
  * @return A [ByteArray] of a [Bitmap]
  */
 suspend fun Bitmap.getByteArray(
@@ -55,7 +52,11 @@ suspend fun Bitmap.getByteArray(
 
     compressImageAndGetByteArray(mimeType, quality)?.let {
         if (it.size > maxFileSizeAllowed && maxFileSizeAllowed !in -1..0) {
-            getByteArray(mimeType, quality - 10, maxFileSizeAllowed)
+            if (quality == 0 || !mimeType.lossyCompressible()) {
+                throw InvalidObjectException ("File size too big.")
+            }
+            // call this method recursively with lower quality
+            byteArray = getByteArray(mimeType, quality - 20, maxFileSizeAllowed)
         } else {
             byteArray = it
         }
@@ -96,6 +97,18 @@ fun String.getCompressFormat(): Bitmap.CompressFormat {
     }
 }
 
+/**
+ * Returns true if lossy compressible format based on mimeType
+ */
+fun String.lossyCompressible(): Boolean {
+    return when {
+        this.contains("jpeg") -> true
+        this.contains("png") -> true
+        this.contains("webp") -> true
+        else -> false
+    }
+}
+
 fun Fragment.dispatchImageSelection(requestCode: Int) {
     val intent = Intent(Intent.ACTION_GET_CONTENT)
     intent.type = "image/*"