Home » Blog » About Outlook » Outlook Error Cannot Send This Item When Replying – Solved

Outlook Error Cannot Send This Item When Replying – Solved

  Rollins Duke
Rollins Duke   
Published: August 21st, 2025 • 6 Min Read

Hello Readers, As Outlook Error Cannot Send These Items When Replying is becoming the most asked queries. So, we have decided to fix this error successfully and users can answer all the emails and also help to maintain workflow and disrupt communication.

This error is not for any specific version of Outlook as it can appear in various Outlook platforms such as Outlook 2016, 2019, 2021, and Microsoft Outlook. Many businesses and professionals rely on Outlook for daily communication and this error may affect productivity.

Table of ContentsHide
  1. Causes of Outlook Error Cannot Send This Item When Replying
  2. How to Fix Outlook Error Cannot Send This Item When Replying
  3. Advanced Solutions to Modify Windows Registry
  4. Alternative Method to Fix Microsoft Outlook Error Message Cannot Send This Item
  5. Preventing Outlook Error Cannot Send This Item When Replying
  6. General Inquiries
  7. Takeaway

Causes of Outlook Error Cannot Send This Item When Replying

  • It mostly happens due to complex HTML formatting in the original message. If a message contains tables, embedded styles or unusual fonts, Outlook may fail to send it when generating a reply.
  • Outlook relies on Add-ins to extend this functionality, but some can interfere with sending replies. Corrupt, outdated or compatible Add-ins may affect the workflow. Causing to block outlook replies with this error Cannot Send This Item.
  • Email signatures that contain images, logos or HTML formatting can cause trouble. If the signature is corrupted, oversized or improperly coded, Outlook may fail to attach correct replies and leading to sending errors.
  • When Outlook is connected to Exchange Server in Cached Exchange Mode, locally stored data can be corrupted. This can result in synchronization issues and in some cases prevent Outlook from sending replies.
  • Sometimes the issue is tied to the Outlook version itself. If the issue is outdated or a recent update introduces bugs, the error may appear frequently. Compatibility issues between older versions and updated Windows can also be the reasons Outlook cannot send email but receive.

How to Fix Outlook Error Cannot Send This Item When Replying

If you are seeing the Outlook Cannot Send Emails But Can Receive Error. There are several solutions available as we have shared below you can try to solve this error:

Method 1. Simplify the Email Format

  1. Open Reply Window in Outlook.
  2. Go to the Format Text tab.
    Click on format text
  3. Select Plain Text or Rich Text instead of complex HTML.

Method 2. Disable Faulty Add-ins

  1. Press Win+R and type Outlook.exe/safe.
    Type safe Outlook
  2. Check issues found or solved here.
  3. If solved then you need to disable faulty Add-ins.
  4. Open Outlook and navigate to the file.
    Click on file
  5. Click on options and choose Add-ins.
    Click on Add-ins
  6. Select COM:Add-ins and press Go.
    Press Go button
  7. Disable suspicious Add-ins and click on OK.
    Disable faulty Add-ins

Method 3. Check and Update Email Signatures

  1. Navigate to file and click on options.
    Click on Options
  2. Tap on Mail and press on Signatures.
    Click on Mail
  3. Edit your signature and remove unnecessary images, large logos, or complex HTML.
  4. Save a clean, text based version with minimal formatting.

Method 4. Update or Repair Outlook

  1. Navigate to file and click on Office Account.
  2. Hit on Update Options and press on Update Now.
    Click on Update Options
  3. Open the Control Panel and click on Mail(Microsoft Outlook).
    Open Control Panel
  4. Click on Email Account and tap on Repair.
    Click on Email Accounts

Method 5. Clear Outlook Cache

  1. Close Outlook completely.
  2. Open the following folder: C:\Users\YourUsername\AppData\Local\Microsoft\Outlook.
  3. Locate and delete OST file and relaunch Outlook to check Error.

Advanced Solutions to Modify Windows Registry

In some cases, Outlook may block certain types of formatting in replies due to registry-level configurations. Edit the Windows Registry can sometimes fix this issues:

  1. Press Win+R and type Regedit and hit Enter.
    Open Regedit
  2. Navigate to: HKEY_CURRENT_USER\Software\Microsoft\Office\16.0\Outlook\Options\Mail
    Click on Software
  3. Create or Edit Dword Value recommended by Microsoft official documentation.
    Edit DWORD value
  4. Relaunch Outlook to test error resolved.

Alternative Method to Fix Microsoft Outlook Error Message Cannot Send This Item

When cached data or hidden message properties cause the Cannot Send This Items error the MFCMAPI tool(a low-level Outlook data editor provided by Microsoft can be used to resolve it:

  1. Download MFCMAPI Tool from the official Microsoft site.
  2. Close Outlook completely before running the tool.
  3. Launch MFCMAPI and choose Session and tap on logon to select your Outlook profile.
  4. Locate the mailbox and navigate to the affected folder e.g., inbox or sent items.
  5. Identify and delete the issues associated with these replies.
  6. Relaunch Outlook to test replying to the same email.

Suggestion: It may happen due to damaged attributes found in your Outlook files. If the explained solution doesn’t work then you can opt for the BitRecover OST Repair Tool as it can easily handle batch Outlook files and offers instant healthy Outlook files. This tool has been completely verified by IT-Admins and also provides a UNICODE resultant PST file to easily access in all the versions of Microsoft Outlook.

Preventing Outlook Error Cannot Send This Item When Replying
  • Avoid complex HTML, oversized signatures, and unnecessary images. Stick to plain or rich text when possible.
  • Install the latest Outlook and Windows Updates regularly to fix bugs and prevent compatibility issues.
  • Disable or remove outdated Add-ins that may conflict with Outlook and cause reply errors.
General Inquiries

Why is Outlook Not Letting Me Reply to Emails?

Outlook may block reply due to complex HTML formatting, corrupted signatures, or faulty Add-ins. Cached data issues or outdated versions of Outlook can also trigger the error. Use Simple formatting, fonts and layout to fix this issue.

Why Does My Outlook Keep Saying Messages Failed to Send?

When Outlook keeps saying a message failed to send and it may be a problem with your connectivity, SMTP Server or corrupted Outlook files. Faulty Add-ins or large attachments may also be the reasons for this error. Check configuration and repair Outlook files to fix this problem.

Why does Outlook Say this Message Cannot be Sent Right Now?

Outlook Says This Message Cannot Be Sent Right Now this error appears when complex formatting, faulty Add-ons or sync issues with your mail server. Outdated Outlook or corrupted Outlook files can also prevent sending Outlook messages.

Takeaway

In this blog post, we have explained all possible solutions to fix Outlook Error Cannot Send This Item When Replying Error. If it’s not done manually then you can opt Automated Approach as it can make healthy Outlook files and it helps to restore Outlook normal functionality.


Live Chat