diff --git a/app/javascript/dashboard/components-next/NewConversation/components/ActionButtons.vue b/app/javascript/dashboard/components-next/NewConversation/components/ActionButtons.vue
index c2971c60d..6def771a0 100644
--- a/app/javascript/dashboard/components-next/NewConversation/components/ActionButtons.vue
+++ b/app/javascript/dashboard/components-next/NewConversation/components/ActionButtons.vue
@@ -171,10 +171,13 @@ const onPaste = e => {
   const files = e.clipboardData?.files;
   if (!files?.length) return;
 
-  Array.from(files).forEach(file => {
-    const { name, type, size } = file;
-    onFileUpload({ file, name, type, size });
-  });
+  // Filter valid files (non-zero size)
+  Array.from(files)
+    .filter(file => file.size > 0)
+    .forEach(file => {
+      const { name, type, size } = file;
+      onFileUpload({ file, name, type, size });
+    });
 };
 
 useEventListener(document, 'paste', onPaste);
diff --git a/app/javascript/dashboard/components/widgets/WootWriter/Editor.vue b/app/javascript/dashboard/components/widgets/WootWriter/Editor.vue
index 7a2a489ac..4b83556de 100644
--- a/app/javascript/dashboard/components/widgets/WootWriter/Editor.vue
+++ b/app/javascript/dashboard/components/widgets/WootWriter/Editor.vue
@@ -676,11 +676,18 @@ function createEditorView() {
         typingIndicator.stop();
         emit('blur');
       },
-      paste: (_view, event) => {
+      paste: (view, event) => {
         if (props.disabled) return;
-        const data = event.clipboardData.files;
-        if (data.length > 0) {
-          event.preventDefault();
+        const { files } = event.clipboardData;
+        if (!files.length) return;
+        event.preventDefault();
+        // Paste text content alongside files (e.g., spreadsheet data from Numbers app)
+        // Numbers app includes invalid 0-byte attachments with text, so we paste the text here
+        // while ReplyBox filters and handles valid file attachments
+        const text = event.clipboardData.getData('text/plain');
+        if (text) {
+          view.dispatch(view.state.tr.insertText(text));
+          emitOnChange();
         }
       },
     },
diff --git a/app/javascript/dashboard/components/widgets/conversation/ReplyBox.vue b/app/javascript/dashboard/components/widgets/conversation/ReplyBox.vue
index 40127aca3..aa67cda0b 100644
--- a/app/javascript/dashboard/components/widgets/conversation/ReplyBox.vue
+++ b/app/javascript/dashboard/components/widgets/conversation/ReplyBox.vue
@@ -692,20 +692,20 @@ export default {
     },
     onPaste(e) {
       // Don't handle paste if compose new conversation modal is open
-      if (this.newConversationModalActive) {
-        return;
-      }
+      if (this.newConversationModalActive) return;
+
       const data = e.clipboardData.files;
       if (!this.showRichContentEditor && data.length !== 0) {
         this.$refs.messageInput?.$el?.blur();
       }
-      if (!data.length || !data[0]) {
-        return;
-      }
-      data.forEach(file => {
-        const { name, type, size } = file;
-        this.onFileUpload({ name, type, size, file: file });
-      });
+
+      // Filter valid files (non-zero size)
+      Array.from(e.clipboardData.files)
+        .filter(file => file.size > 0)
+        .forEach(file => {
+          const { name, type, size } = file;
+          this.onFileUpload({ name, type, size, file });
+        });
     },
     toggleUserMention(currentMentionState) {
       this.showUserMentions = currentMentionState;