diff --git a/src/views/app/detail-panel/edit/parts/edit-view-header.tsx b/src/views/app/detail-panel/edit/parts/edit-view-header.tsx
index 9fab01aee..7984b9cbf 100644
--- a/src/views/app/detail-panel/edit/parts/edit-view-header.tsx
+++ b/src/views/app/detail-panel/edit/parts/edit-view-header.tsx
@@ -1,3 +1,4 @@
+/* eslint-disable no-nested-ternary */
 /*
  * SPDX-FileCopyrightText: 2022 Zextras <https://www.zextras.com>
  *
@@ -205,9 +206,20 @@ const EditViewHeader: FC<PropType> = ({
 
 	const createModal = useModal();
 	const sendMailAction = useCallback(() => {
-		if (editor?.subject) {
-			sendMailCb();
-		} else {
+		const attachWords = [
+			t('messages.modal.send_anyway.attach', 'attach'),
+			t('messages.modal.send_anyway.attachment', 'attachment'),
+			t('messages.modal.send_anyway.attachments', 'attachments'),
+			t('messages.modal.send_anyway.attached', 'attached'),
+			t('messages.modal.send_anyway.attaching', 'attaching'),
+			t('messages.modal.send_anyway.enclose', 'enclose'),
+			t('messages.modal.send_anyway.enclosed', 'enclosed'),
+			t('messages.modal.send_anyway.enclosing', 'enclosing')
+		];
+		const isattachWordsPresent = attachWords.some((el) =>
+			editor.text[0].toLowerCase().includes(el)
+		);
+		if ((isattachWordsPresent && !editor?.attachmentFiles.length) || !editor?.subject) {
 			const closeModal = createModal({
 				title: t('header.attention', 'Attention'),
 				confirmLabel: t('action.ok', 'Ok'),
@@ -226,19 +238,26 @@ const EditViewHeader: FC<PropType> = ({
 				children: (
 					<StoreProvider>
 						<Text overflow="break-word" style={{ paddingTop: '16px' }}>
-							{t(
-								'messages.modal.send_anyway.first',
-								"Email subject is empty and you didn't attach any files."
-							)}
+							{isattachWordsPresent && !editor?.attachmentFiles.length && !editor?.subject
+								? t(
+										'messages.modal.send_anyway.no_subject_no_attachments',
+										'Email subject is empty and you didn’t attach any files.'
+								  )
+								: !editor?.subject
+								? t('messages.modal.send_anyway.no_subject', 'Email subject is empty.')
+								: t('messages.modal.send_anyway.no_attachments', 'You didn’t attach any files.')}
 						</Text>
+
 						<Text overflow="break-word" style={{ paddingBottom: '16px' }}>
 							{t('messages.modal.send_anyway.second', 'Do you still want to send the email?')}
 						</Text>
 					</StoreProvider>
 				)
 			});
+		} else {
+			sendMailCb();
 		}
-	}, [editor?.subject, createModal, sendMailCb]);
+	}, [editor?.attachmentFiles.length, editor?.subject, editor.text, createModal, sendMailCb]);
 
 	const onSave = useCallback(() => {
 		saveDraftCb(editor);
diff --git a/translations/en.json b/translations/en.json
index 50c7dab2a..59d9fb223 100644
--- a/translations/en.json
+++ b/translations/en.json
@@ -464,7 +464,17 @@
                 "second": "The e-mail will appear as originally intended for the new recipient"
             },
             "send_anyway": {
-                "first": "Email subject is empty and you didn't attach any files.",
+                "attach": "attach",
+                "attached": "attached",
+                "attaching": "attaching",
+                "attachment": "attachment",
+                "attachments": "attachments",
+                "enclose": "enclose",
+                "enclosed": "enclosed",
+                "enclosing": "enclosing",
+                "no_attachments": "You didn’t attach any files.",
+                "no_subject": "Email subject is empty.",
+                "no_subject_no_attachments": "Email subject is empty and you didn’t attach any files.",
                 "second": "Do you still want to send the email?"
             }
         },