The text box suddenly stopped working in Outlook (desktop) but works fine in Word

Question

The text box function stopped working in Outlook. I can click on the link, but the draw tool will not populate in addition to any preloaded options. The text box is only tool not working.

Answer 1

Hello, I might I found a work around. That feature still works on the office version 2408, but not in the 2508.

Can you please try to:

Open New email > Insert > Click on WordART > Select any > While in the "Shape Format " tab, click on the Draw to text button that is in the top right of the " Insert Shapes" session.

A quick way to access this feature is to Right click the "Insert Shapes" and click on ADD to quick access toolbar.

A quick access button will appear on the top right just above the "File" "Message" "..." when you open a new email.

Hope this helps.

Answer 2

Hi @Naples, Pat J (DMV),

Thank you for reaching out regarding the issue you are experiencing with the Text Box feature in Outlook.

Based on your description, this may be related to how Classic Outlook handles text boxes and drawing features in certain compose modes and message formats.

To help identify the cause of the issue, you can review and try the following steps:

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1/ Confirm the email format is set to HTML

In Outlook, text boxes, shapes, and several options under the Insert tab are only available when the message is composed in HTML format.

To check this, you can:

• Open the email you are composing.
• On the ribbon, go to Format Text > select HTML.

• Return to the Insert tab and try Text Box > Draw Text Box again.

 

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2/ Pop out the message into its own window

• If you are replying or forwarding within the Reading Pane, select Pop Out from the message header.

• Once the message opens in a separate window, go to Insert > Text Box > Draw Text Box.
• Click inside the message body and attempt to draw the text box.

 

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3/ Test Outlook in Safe Mode

• Press the Windows key + R to open the Windows Run dialog.
• In the Open box, type Outlook /safe, then choose OK.
• In the Choose Profiles dialog box, accept the default setting of Outlook and choose OK.

• If prompted, enter your password and choose Accept.

If Outlook is able to start in safe mode, then the problem is likely with one of your add-ins. You'll need to disable all of your add-ins before restarting Outlook, as described in the following procedures:

• In the upper-left corner of Outlook, choose File > Options > Add-ins.
• At the bottom of the View and manage Office Add-ins, make sure the Manage box shows COM Add-ins, and then choose Go.

• Take a screenshot of the selected add-ins listed under Available Add-ins and save the image to a location of your choice.
• After you've captured the titles of the selected add-ins, clear all selected check boxes, and then choose OK. Note: Please click a check box to clear it. Don't select an add-in and choose Remove.
• Choose File > Exit.

If the program loads properly, it's likely that one of your add-ins is the source of the issue and you need to identify which one. To determine which add-in is the problem, enable one add-in at a time:

• Press the Windows key + R to open the Run dialog.
• In the Open box, type Outlook.
• In the upper-left corner of Outlook, choose File > Options > Add-ins.
• Select the check box next to an add-in you want to re-enable and then choose OK.
• Repeat all steps until you've re-enabled all of the original add-ins and revealed the source of the error.

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4/ Repair the Office installation

If the issue persists, repairing the Office installation may resolve underlying application issues. For reference: Repair an Office application - Microsoft Support

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5/ Contact Microsoft Support

If the issue continues after applying these steps, the best next step would be to have your IT administrator open a support ticket with Microsoft via the admin center. A technical support engineer can then initiate a remote session, review backend settings, and run diagnostics. If needed, they can escalate the case to specialized engineering teams who are well-equipped to perform advanced troubleshooting and provide targeted solutions.

As moderators, our primary goal is to provide helpful guidance and support through general troubleshooting steps. While we don’t have access to internal systems or administrative tools required to resolve account-specific or backend issues, we truly appreciate your understanding of these limitations. We genuinely hope the information we share helps point you in the right direction, and we're always here to assist as much as we can within our scope.

For guidance on how to request support, please share the guidance in this link with your admin: Get support - Microsoft 365 admin. 

I hope this information is useful. Thank you for taking the time to raise this question. If you need any further clarification or assistance, please feel free to leave a comment under this post.

If you find my post useful, kindly consider upvoting it. Doing so can assist others in the community who may have similar questions in finding solutions more quickly.

Thank you for your contributions to the forum.

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Answer 3

The behavior is consistent with a damaged or misbehaving Office/Outlook component rather than a feature change, especially since the same Text Box feature still works in Word.

Use these steps in order and test the Text Box in Outlook after each:

1. Restart Outlook and Windows
   • Close Outlook.
   • Restart Windows (not just sign out) to clear any incomplete updates.
   • Open Outlook and test Insert → Text Box → Draw Text Box in a new message.
2. Disable add-ins in Outlook Some add-ins can interfere with the editor used by Outlook.
   1. Start Outlook in safe mode (for example, run outlook.exe /safe).
   2. Create a new email and test the Text Box.
      • If it works in safe mode, an add-in is likely the cause.
   3. In normal Outlook, go to File → Options → Add-ins.
   4. At the bottom, in Manage, choose COM Add-ins → Go.
   5. Uncheck all add-ins, then re-enable them one by one, restarting Outlook each time, until the Text Box stops working again. Leave the problematic add-in disabled or update/remove it.
   Older add-ins such as ABBYY FineReader or Dragon Naturally Speaking are known to cause issues and should be unchecked first.
3. Repair Office If add-ins are not the cause, repair the Office installation.
   1. Close all Office apps.
   2. Open Settings → Apps → Installed apps (or Apps & features).
   3. Select Microsoft Office (or Microsoft 365 Apps) → Modify.
   4. Run a Quick Repair first and test.
   5. If the issue persists, run an Online Repair, which can effectively reinstall Office and fix corrupted components.
4. If repair does not help
   • Completely uninstall Office using the standard uninstall method or the Microsoft 365 uninstall troubleshooter, restart the PC, then reinstall Office from the Microsoft account or organizational portal.

These steps address the most common causes of individual Office features (like Text Box in Outlook’s editor) suddenly stopping while still working in other apps.

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References:

• I get a "stopped working" error when I start Office applications on my PC
• Outlook, Word, or OneNote unexpectedly close when typing
• How to fix my MS Word? - Microsoft Q&A
• we are sorry, but word has run into an error that is preventing it from working correctly. Word will need to be closed as a result. Would you like us to repair now? - Microsoft Q&A