Overview: If you are facing an Outlook attachment reminder not working problem, then refer to our guide for instant fix. Here, you can try these methods to troubleshoot the problem.

Sometimes, users miss attaching a document before sending an email. Many people rely on the built-in reminder available in Outlook that is designed to alert the person sending the email. Especially when there is a mention of the possible attachment in the email, but none of them is physically included. There are times when the notification fails to appear even though it is activated. This can happen because of several reasons that we will discuss in the coming section.

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Outlook Attachment Warning Not Working? Reasons Behind

There are multiple factors connected with the Outlook attachment reminder not working problem.

  • The attachment warning feature has been turned off
  • You need to toggle it off and turn it back on the settings part
  • It is because you are using a different version of Outlook which can differ with the expected one
  • Email features might be subject to interference from an Outlook plug-in
  • New Outlook might face issues due to caching or session issues
  • The email message doesn’t have a string that Outlook recognizes, when it’s related to attachments
  • Due to inappropriate behavior of the feature in New, Classic, and Outlook on the web

Also Read: How to Fix Outlook Attachment Preview Not Working?

A Better Way to Extract Existing Outlook Attachments in Bulk

After you have fixed your Outlook attachment reminder not working problem, if you want to search, find, and extract attachments from large Outlook mailboxes. The best option is SysTools Outlook Attachment Extractor Software instead of relying on the reminder function. It allows you to extract the attachments straight from Outlook data files, and thus eliminate the need to access each email and save files individually. It works with PST, OLM, OST, OLK, MSG, and BAK files depending on the platform and supported configuration.

When to Use:

  • Having attachments in multiple Outlook data files
  • Want to extract data in bulk
  • If you have inline images, and regular attachments
  • Maintain exact folder structure
  • Users can filter in terms of date, & time
  • Reduce your manual task and you can easily work with large mailboxes
  • Gives you a proper report of the entire process

Outlook Attachment Reminder Not Working – 8 Manual Fixes

Try every method one by one in order to turn on attachment reminder in Outlook.

#1. Turn On Attachment Warning in Classic Outlook

If you are a Classic Outlook user, then try this method. In this, you need to confirm if the warning for missing attachments is turned on. Now, try these simple steps to fix Outlook attachment reminder not working.

  • Firstly, launch Outlook
  • Next, click on File
  • There, choose Options
  • After that, go to the Mail tab in the dialog box
  • Scroll down to the Send messages section
  • Locate the option for Warn me when I send a message that may be missing an attachment
  • Now, Ensure that the option is enabled
  • Just click on OK
  • Lastly, close and reopen Outlook once again

Now, create a test email and write some words like:

“I have attached the document for your review.”

Now, don’t attach any file and try to send the email. If the warning pops up, then the feature is working.

#2. Enable the Settings Off & On Again

At times, just ticking the checkbox is not enough. There is a user’s report on Microsoft Q&A that talks about this problem. You can solve the problem of Outlook attachment reminder not working by following the below steps:

  • Go to File > Options > Mail
  • Next, uncheck the attachment warning checkbox
  • Press OK
  • After that, shut down Outlook completely
  • You need to reopen it
  • Go to view the same setting again
  • Now, re-check the warning checkbox
  • Now, tap on OK
  • To check, you can send an email without attaching any files

#3. Check the Settings in New Outlook

In case you are making use of the New Outlook for Windows, then the settings could be found at a different location.

  • Start by launching New Outlook
  • Next, tap on the Settings icon
  • Choose Mail
  • Then, select the relevant attachment settings
  • Look for the option that says “warn me when I send an email that might have an attachment missing”
  • Now, enable that feature once
  • After that, close the settings option
  • Compose a new email and verify if the settings work

At the moment, Microsoft is keeping a record of its forgotten attachment warning associated with New Outlook. This alert occurs whenever the email mentions an attachment, but there is nothing inside the mail.

#4. Try Common Terms Related to Attachments

The feature does not specify that each sentence or situation should be understood.

As an example, you may try sending a simple statement:

“This is an attached invoice.”

Do not attach any invoice and press send. Some other statements you can try are:

“Please find the attached document”

“I have attached the report”

“See the file attached for your review”

“Please see the attachment”

If Outlook issues the notice on the above examples, but not on the usual email you send. The trouble could be related to how Outlook interprets the text of your message.

Important for New Outlook:

According to Microsoft, the forgotten attachment notification in New Outlook reveals itself when the text of an email is formatted in English. The application itself may be set in a different language, but the text of your email must be according to the required format. So, that the warning can be activated.

#5. Check Whether an Add-in is the Problem

The add-ins can be the problem behind Outlook attachment reminder not working. According to Microsoft, COM add-ins can lead to issues in Classic Outlook as well.

1. To run Outlook without the add-ins, you need to run it in Safe Mode.
2. Press the Windows + R button together
3. Next, you need to type:

outlook.exe /safe

4. Press on Enter
5. Create a new email
6. Write something about the attachment, but do not actually attach anything
7. Click on the Send button

If the attachment warning appears in Safe Mode, an add-in is creating the problem. You can disable the unwanted add-ins and try using Outlook again.

#6. Refresh New or Web Outlook

If you are using the New or Web Outlook, the issue may not be from the mailbox itself.

  • Firstly, disable the attachment warning feature
  • Log out from Outlook
  • Shut down the browser or Outlook window
  • If you are using Outlook on the web, you need to delete the browser cache
  • Launch Outlook
  • Now, you need to log in again
  • Reactivate the attachment warning feature
  • Attempt to send a test email

In a recent question-and-answer on Microsoft’s website, this method was suggested for cases where the setup is on but the warning does not pop up.

#7. Update Outlook & Microsoft 365

An outdated version of Outlook can lead to an Outlook attachment reminder not working problem.

For Classic Outlook:

  • Start Outlook
  • Click on the File tab and then Office Account
  • After that, choose Update Options
  • Press on Update Now
  • Fetch any pending updates
  • Lastly, reopen Outlook

After updating, verify whether the attachment alert will still fail.

It is equally important to check if the same issue is present in Outlook Web. If the alert works in web-based email, but is ineffective in the desktop Outlook application. The issue is more connected to Outlook desktop installation, profile, or add-ins. Also,

#8. Test the Same Email in Another Outlook Version

  • Firstly, access the same email using New, Classic, & Web versions of Outlook
  • Determine, if the alert regarding attachments comes up or not
  • It appears when used on the internet, but does not show when used on a computer. Just check the settings
  • Whenever your Classic Outlook shows the alert, and New Outlook doesn’t. You just compare the options available in New Outlook
  • If the alert does not appear in either version, then check the account or the email
  • Evaluate the various situations to find whether the problem is related to the versions of Outlook you are using

Limitations of Outlook Attachment Reminder

Even after following the above steps to fix the Outlook attachment reminder not working issue, the feature is still not entirely reliable.

  • It is not sure that all the missing attachments will be detected
  • Warning may never show up if the email does not state that it contains attachment
  • In New Outlook, the feature applies only to the English language written content
  • Cannot verify through reminders that the correct file is attached
  • The reminder will only help you be notified of not sending your email before.
  • Rather than helping you get back lost attachments

Conclusion

By correcting problems such as checking warning settings, using appropriate words related to attachments, checking language settings, restarting Outlook, running it in Safe Mode, disabling add-ons, and repairing Microsoft 365. You can easily fix Outlook attachment reminder not working.

But, this reminder does not indicate all missing files. To help you find, and extract attachments from private emails, particularly from large or many Outlook data files. Going with our automated solution is the right choice. As you may face several disadvantages while following manual steps, the tool allows you to retrieve file attachments in bulk and apply necessary filters and folders.