diff --git a/Tusker/Screens/Compose/Attachments/ComposeAttachmentTableViewCell.swift b/Tusker/Screens/Compose/Attachments/ComposeAttachmentTableViewCell.swift
index 5d95eac2..2de3fe67 100644
--- a/Tusker/Screens/Compose/Attachments/ComposeAttachmentTableViewCell.swift
+++ b/Tusker/Screens/Compose/Attachments/ComposeAttachmentTableViewCell.swift
@@ -82,8 +82,8 @@ class ComposeAttachmentTableViewCell: UITableViewCell {
 
 extension ComposeAttachmentTableViewCell: UITextViewDelegate {
     func textViewDidChange(_ textView: UITextView) {
-        delegate?.attachmentDescriptionChanged(self)
         attachment.attachmentDescription = textView.text
         updateDescriptionPlaceholderLabel()
+        delegate?.attachmentDescriptionChanged(self)
     }
 }
diff --git a/Tusker/Screens/Compose/Attachments/ComposeAttachmentsViewController.swift b/Tusker/Screens/Compose/Attachments/ComposeAttachmentsViewController.swift
index 0a06b9fe..be3bfee3 100644
--- a/Tusker/Screens/Compose/Attachments/ComposeAttachmentsViewController.swift
+++ b/Tusker/Screens/Compose/Attachments/ComposeAttachmentsViewController.swift
@@ -25,13 +25,14 @@ class ComposeAttachmentsViewController: UITableViewController {
     var attachments: [CompositionAttachment] = [] {
         didSet {
             delegate?.composeSelectedAttachmentsDidChange()
+            delegate?.composeRequiresAttachmentDescriptionsDidChange()
             updateAddAttachmentsButtonEnabled()
         }
     }
     
     var requiresAttachmentDescriptions: Bool {
         if Preferences.shared.requireAttachmentDescriptions {
-            return !attachments.allSatisfy { $0.description.trimmingCharacters(in: .whitespacesAndNewlines).isEmpty }
+            return attachments.contains { $0.attachmentDescription.trimmingCharacters(in: .whitespacesAndNewlines).isEmpty }
         } else {
             return false
         }