diff --git a/app/src/main/kotlin/com/simplemobiletools/smsmessenger/activities/ThreadActivity.kt b/app/src/main/kotlin/com/simplemobiletools/smsmessenger/activities/ThreadActivity.kt
index e426b931..629e6ed8 100644
--- a/app/src/main/kotlin/com/simplemobiletools/smsmessenger/activities/ThreadActivity.kt
+++ b/app/src/main/kotlin/com/simplemobiletools/smsmessenger/activities/ThreadActivity.kt
@@ -671,6 +671,13 @@ class ThreadActivity : SimpleActivity() {
                     if (compressedUri != null) {
                         attachmentSelections[originalUriString] = AttachmentSelection(compressedUri, false)
                         loadAttachmentPreview(attachmentView, compressedUri)
+                    } else {
+                        toast(R.string.compress_error)
+                        thread_attachments_wrapper.removeView(attachmentView)
+                        attachmentSelections.remove(originalUriString)
+                        if (attachmentSelections.isEmpty()) {
+                            thread_attachments_holder.beGone()
+                        }
                     }
                     checkSendMessageAvailability()
                     attachmentView.thread_attachment_progress.beGone()
diff --git a/app/src/main/kotlin/com/simplemobiletools/smsmessenger/helpers/ImageCompressor.kt b/app/src/main/kotlin/com/simplemobiletools/smsmessenger/helpers/ImageCompressor.kt
index aa58387e..66ad7e7b 100644
--- a/app/src/main/kotlin/com/simplemobiletools/smsmessenger/helpers/ImageCompressor.kt
+++ b/app/src/main/kotlin/com/simplemobiletools/smsmessenger/helpers/ImageCompressor.kt
@@ -106,7 +106,11 @@ class ImageCompressor(private val context: Context) {
         private var iteration: Int = 0
 
         fun isSatisfied(imageFile: File): Boolean {
-            return imageFile.length() <= maxFileSize || iteration >= maxIteration
+            // If size requirement is not met and iteration is maxed
+            if(iteration >= maxIteration && imageFile.length() >= maxFileSize) {
+                throw Exception("Unable to compress image to targeted size")
+            }
+            return imageFile.length() <= maxFileSize
         }
 
         fun satisfy(imageFile: File): File {
diff --git a/app/src/main/res/values/strings.xml b/app/src/main/res/values/strings.xml
index 74042531..658870b1 100644
--- a/app/src/main/res/values/strings.xml
+++ b/app/src/main/res/values/strings.xml
@@ -19,6 +19,7 @@
     <string name="pin_conversation">Pin to the top</string>
     <string name="unpin_conversation">Unpin</string>
     <string name="forward_message">Forward</string>
+    <string name="compress_error">Unable to compress image to selected size</string>
     <!-- New conversation -->
     <string name="new_conversation">New conversation</string>
     <string name="add_contact_or_number">Add Contact or Number…</string>