diff --git a/mealie/services/email/email_senders.py b/mealie/services/email/email_senders.py
index 370441c59efb..ecb840c6f9c5 100644
--- a/mealie/services/email/email_senders.py
+++ b/mealie/services/email/email_senders.py
@@ -3,6 +3,10 @@ import typing
 from abc import ABC, abstractmethod
 from dataclasses import dataclass
 from email import message
+from email.utils import formatdate
+from uuid import uuid4
+
+from html2text import html2text
 
 from mealie.services._base_service import BaseService
 
@@ -36,7 +40,19 @@ class Message:
         msg["Subject"] = self.subject
         msg["From"] = f"{self.mail_from_name} <{self.mail_from_address}>"
         msg["To"] = to
+        msg["Date"] = formatdate(localtime=True)
         msg.add_alternative(self.html, subtype="html")
+        msg.add_alternative(html2text(self.html), subtype="plain")
+
+        try:
+            message_id = f"{uuid4()}@{self.mail_from_address.split('@')[1]}"
+        except IndexError:
+            # this should never happen with a valid email address,
+            # but we let the SMTP server handle it instead of raising it here
+            message_id = f"{uuid4()}@{self.mail_from_address}"
+
+        msg["Message-ID"] = message_id
+        msg["MIME-Version"] = "1.0"
 
         if smtp.ssl:
             with smtplib.SMTP_SSL(smtp.host, smtp.port) as server:
diff --git a/poetry.lock b/poetry.lock
index 6b982c68b841..c3e40c30621a 100644
--- a/poetry.lock
+++ b/poetry.lock
@@ -708,6 +708,17 @@ files = [
 [package.dependencies]
 lxml = "*"
 
+[[package]]
+name = "html2text"
+version = "2020.1.16"
+description = "Turn HTML into equivalent Markdown-structured text."
+optional = false
+python-versions = ">=3.5"
+files = [
+    {file = "html2text-2020.1.16-py3-none-any.whl", hash = "sha256:c7c629882da0cf377d66f073329ccf34a12ed2adf0169b9285ae4e63ef54c82b"},
+    {file = "html2text-2020.1.16.tar.gz", hash = "sha256:e296318e16b059ddb97f7a8a1d6a5c1d7af4544049a01e261731d2d5cc277bbb"},
+]
+
 [[package]]
 name = "html5lib"
 version = "1.1"
@@ -2013,7 +2024,6 @@ files = [
     {file = "PyYAML-6.0.1-cp311-cp311-win_amd64.whl", hash = "sha256:bf07ee2fef7014951eeb99f56f39c9bb4af143d8aa3c21b1677805985307da34"},
     {file = "PyYAML-6.0.1-cp312-cp312-macosx_10_9_x86_64.whl", hash = "sha256:855fb52b0dc35af121542a76b9a84f8d1cd886ea97c84703eaa6d88e37a2ad28"},
     {file = "PyYAML-6.0.1-cp312-cp312-macosx_11_0_arm64.whl", hash = "sha256:40df9b996c2b73138957fe23a16a4f0ba614f4c0efce1e9406a184b6d07fa3a9"},
-    {file = "PyYAML-6.0.1-cp312-cp312-manylinux_2_17_aarch64.manylinux2014_aarch64.whl", hash = "sha256:a08c6f0fe150303c1c6b71ebcd7213c2858041a7e01975da3a99aed1e7a378ef"},
     {file = "PyYAML-6.0.1-cp312-cp312-manylinux_2_17_x86_64.manylinux2014_x86_64.whl", hash = "sha256:6c22bec3fbe2524cde73d7ada88f6566758a8f7227bfbf93a408a9d86bcc12a0"},
     {file = "PyYAML-6.0.1-cp312-cp312-musllinux_1_1_x86_64.whl", hash = "sha256:8d4e9c88387b0f5c7d5f281e55304de64cf7f9c0021a3525bd3b1c542da3b0e4"},
     {file = "PyYAML-6.0.1-cp312-cp312-win32.whl", hash = "sha256:d483d2cdf104e7c9fa60c544d92981f12ad66a457afae824d146093b8c294c54"},
@@ -2938,4 +2948,4 @@ pgsql = ["psycopg2-binary"]
 [metadata]
 lock-version = "2.0"
 python-versions = "^3.10"
-content-hash = "3af89a4b335d71028761cbd6c2293eda5dbd0d0518d1dacd60440ef5401ba873"
+content-hash = "80b15507db71f3e7f66c8391405aa2a47f901fb94296006495ed47027ee8d88d"
diff --git a/pyproject.toml b/pyproject.toml
index 0dd50d1112d1..602115a892ad 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -44,6 +44,7 @@ beautifulsoup4 = "^4.11.2"
 isodate = "^0.6.1"
 text-unidecode = "^1.3"
 rapidfuzz = "^3.2.0"
+html2text = "^2020.1.16"
 
 [tool.poetry.group.dev.dependencies]
 black = "^23.7.0"