3 Quick Fixes to Microsoft Outlook “Cannot Send This Item”

Get stuck on the Outlook message “Cannot send this item”? Don’t worry. Learn how to fix it with three easy ways here.


By Lily Updated on December 20, 2023

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User case: Outlook message “Cannot send this item”

“Hi, As of yesterday my Outlook is popping the above message every time I try to reply or forward a mail as HTML. I even try to save the message and send it after but even that does not work. Can you please help ?”

Outlook Cannot Send This Item

Sometimes, the error “Cannot send this item” in Outlook reply or forward happens when the original email contains long links. You may get caught in the problem if the 2085th character in a link is an escaped character or the long URLs are processed with SafeLinks. How to get rid of this problem? Please read on.

How to fix Microsoft Outlook “Cannot send this item”

According to Microsoft, there are three workarounds to help you solve Outlook 2019 “Cannot send this item”. These methods also apply to Outlook 2016/2013/2010/2007, etc.

AOMEI Backupper

It is recommended to backup your email data in case of unexpected errors.

Fix 1: Change the email format from HTML to Rich Text

  1. In the message, click Reply, Reply All, or Forward.
  2. If you’re working in the Reading Pane, click Pop Out. If not, skip to the next step.
  3. In the message window, click Format Text > Rich Text.

Format Text

👉 HTML: it is the default message format in Outlook. It is also the best format to use when you want to create messages that look like traditional documents.
👉 Plain Text: it works for all email programs, but it doesn’t support bold or italic text, colored fonts, or other text formatting. It also doesn't support showing pictures inside the message, although you can include pictures as attachments.
👉 Rich Text: it is a Microsoft format that’s supported only by Outlook and Microsoft Exchange Client versions 4.0 and 5.0. With Rich Text Format (RTF), you can format text with bullets, align text, and add linked objects, etc. Attachments in an RTF message appear as icons within the message body.

Fix 2: Remove any long links in the body

As the Outlook “Cannot send this item” issue is caused by long links in the original message, you can fix it by simply removing the long links in the body before replying or forwarding.

Fix 3: Reply using Outlook Web App (OWA)

When you can’t reply to an email that has long links in the body using Outlook desktop app, you may try again using Outlook web app.

Backup your email data with the best Outlook backup software

Outlook contains plenty of important data, including mail items, appointments, contacts, tasks, and notes. To avoid data loss caused by accidental deletion, data corruption, a ransomware attack or other unexpected situations, it is suggested to backup Outlook data regularly.

AOMEI Backupper Professional is the best Outlook backup software for Windows PC. With an intuitive interface, even a computer novice can handle Outlook backup tasks effortlessly.

✦ It enables you to backup all data in Outlook to various backup storage devices, such as an internal/external hard drive, USB flash drive, and NAS device, etc.
✦ It supports Outlook, Gmail, Hotmail, and any other email accounts added into Outlook client.
✦ It offers the “Schedule Backup” feature to help you backup your email data automatically.
✦ It allows you to run incremental or differential backup to reduce backup time and storage space taken by the backup image.

To backup Outlook data in Windows 11/10/8/7, use the following steps:

Step 1. Add the email account you want to backup to Outlook.

  • If you're adding your first email account, go to Start > Outlook, enter your email address and click Connect.

Add Account Oulook

  • If you’re adding an additional email account, go to Start > Outlook > File > Add Account. The rest steps are the same as you add the first email account.

Add Account

Step 2. Download and install AOMEI Backupper on your PC. Launch the program, click Backup and select Outlook Backup.

Download Free Trial Win 11/10/8.1/8/7/XP
Secure Download

Outlook Backup

Step 3. Click Add Outlook Data. In the popup window, select the items to be backed up. You can choose the whole email account or several subfolders under it.

Add Outlook Data

Step 4. Select a destination path to save the backup image.

Select Destination Path

Step 5. Customize your backup task with Options, Schedule Backup and Backup Scheme as necessary. Finally, click Start Backup to begin backing up your Outlook data.

Start Backup


This page offers three ways to solve Microsoft Outlook “Cannot send this item”. To protect your Outlook data safety, you can create Outlook backup with AOMEI Backupper. It enables you to backup all of your emails, contacts, notes, calendars, and tasks in Outlook to different locations. What’s more, it is powerful C drive clone software that enables you to clone C drive to a larger SSD. Try it now to discover more!

Lily · Editor
Lily Green joined AOMEI in 2018 and has since become a professional in the areas of data protection and data transfer. She is committed to helping users protect their precious computer data and troubleshoot Windows system errors. She consistently stays vigilant about the latest trends in technology, guaranteeing that the given information aligned with the ongoing advancements in the field.