When replying in Outlook, preserving attachments requires changing a setting in the message format options. This guide explains how to keep attachments when replying in Outlook, covering both classic and new versions. You’ll learn quick steps to avoid losing attached files every time you hit reply.
Many users find that attachments vanish when they reply to an email. This happens because Outlook defaults to stripping attached files from replies. But you can fix this with a simple adjustment.
We’ll walk through the exact settings to change. Whether you use Outlook 365, 2021, or the web version, these methods work. No more re-attaching files manually.
Why Attachments Disappear When Replying In Outlook
Outlook treats replies as new messages by default. It removes attachments to keep replies clean and reduce file size. This is intentional, but not always helpful.
When you reply to an email with attachments, Outlook assumes you want to respond without those files. It strips them to prevent accidental sharing or bloated email threads. However, this can be frustrating when you need to keep the attachments for context.
The setting that controls this behavior is buried in the message format options. Changing it tells Outlook to include original attachments in replies. Let’s find that setting now.
How To Keep Attachments When Replying In Outlook
This section covers the main method for Outlook desktop versions. Follow these steps to preserve attachments in replies.
Step 1: Open Outlook Options
Launch Outlook on your computer. Click the File tab in the top-left corner. A menu will appear.
Select Options from the list. This opens the Outlook Options dialog box. It contains all major settings for the application.
Step 2: Navigate To Mail Settings
In the Outlook Options window, click Mail on the left sidebar. This section controls email composition and reply behavior.
Scroll down to the Replies and forwards section. You’ll see a few options here that affect how replies are formatted.
Step 3: Change The Reply Setting
Look for the dropdown menu labeled When replying to a message. Click it to see the options.
Select Include original message text from the list. This setting keeps the original email content, including attachments, in your reply.
If you see Attach original message, choose that instead. It attaches the entire original email as an attachment, preserving everything.
Click OK to save your changes. Now when you reply, attachments should stay in the email.
Step 4: Test The Setting
Send yourself a test email with an attachment. Open it and click Reply. Check if the attachment appears in the reply window.
If it does, the setting worked. If not, double-check that you selected the right option. Some Outlook versions have slight differences.
Alternative Method: Use The Ribbon
If the options menu doesn’t work, try this quick alternative. It uses the ribbon toolbar in the reply window.
Step 1: Open A Reply
Open an email with an attachment. Click Reply to open the reply composition window.
Step 2: Access The Attach Options
In the reply window, look for the Include group on the Message tab. You’ll see an Attach File button.
Click the dropdown arrow next to Attach File. Select Attach Item from the menu.
Step 3: Attach The Original Email
A dialog box appears. Choose Outlook Item from the left pane. Find the original email in your inbox.
Select it and click OK. The original email, with all attachments, is now attached to your reply.
This method works for individual replies but isn’t automatic. You’ll need to do it each time.
How To Keep Attachments In Outlook Web App
The web version of Outlook works differently. Here’s how to preserve attachments when replying online.
Step 1: Open The Email
Log into Outlook.com or your work webmail. Open the email that has attachments.
Step 2: Click Reply
Click the Reply button. The reply window opens with the original message quoted below.
Look for the attachments in the quoted section. They should appear as clickable links or icons.
Step 3: Drag Attachments To The Top
If attachments are missing, drag them from the quoted area to the top of the reply. This adds them as separate attachments.
Alternatively, click the paperclip icon in the reply toolbar. Select Browse this computer and re-upload the files.
This manual method is the only option in Outlook Web App. There’s no automatic setting to keep attachments.
How To Keep Attachments In Outlook For Mac
Mac users have a slightly different process. Here’s how to set it up in Outlook for Mac.
Step 1: Open Preferences
Launch Outlook on your Mac. Click Outlook in the top menu bar. Select Preferences.
Step 2: Find The Reply Setting
In the Preferences window, click Composing. This section controls email composition settings.
Look for the When replying to messages dropdown. Click it and select Include original message.
Step 3: Save And Test
Close the Preferences window. The setting saves automatically. Test it by replying to an email with an attachment.
If attachments don’t appear, try selecting Attach original message instead. This attaches the entire email as a file.
Troubleshooting Common Issues
Sometimes the setting doesn’t work as expected. Here are common problems and fixes.
Attachments Still Missing After Changing Settings
Check if you selected the correct option. Some versions have Include original message text and Attach original message as separate choices. Try the other one.
Also, ensure you clicked OK to save. If you closed the window without saving, the change won’t apply.
Setting Resets After Outlook Update
Outlook updates can reset your preferences. After an update, check the reply setting again. Reapply it if needed.
To avoid this, note the setting location. You can quickly restore it after updates.
Attachments Appear But Are Not Downloadable
This usually happens with linked files from OneDrive or SharePoint. The attachment is a link, not a file. Recipients need access permissions to download it.
To fix this, download the attachment first, then re-attach it as a regular file. This ensures it’s fully included.
Best Practices For Managing Attachments In Replies
Keeping attachments in replies is useful, but use it wisely. Here are some tips.
- Only keep attachments that are relevant to the reply. Remove unnecessary files to reduce clutter.
- Consider the file size. Large attachments can slow down email delivery and fill inboxes quickly.
- Use the Attach original message option for important threads. It preserves the entire context.
- For sensitive files, double-check that you’re not sharing attachments accidentally. Reply to the right people.
- If you frequently need attachments, create a rule to automatically include them. This saves time.
How To Create A Rule For Attachments
Rules automate attachment handling. Here’s how to set one up in Outlook desktop.
Step 1: Open Rules
Click File > Manage Rules & Alerts. A new window opens.
Step 2: Create A New Rule
Click New Rule. Select Apply rule on messages I receive.
Step 3: Set Conditions
Choose conditions like with attachments or from specific senders. This targets the rule.
Step 4: Set Actions
Select an action like forward it or flag it. For replies, you can’t directly set attachment behavior with rules. But you can use rules to organize emails before replying.
Rules are more useful for automating other tasks. For attachment preservation, stick to the settings method.
Keyboard Shortcuts For Quick Attachment Handling
Speed up your workflow with these shortcuts.
- Ctrl + R (Windows) or Cmd + R (Mac) to reply to an email.
- Ctrl + Shift + R (Windows) to reply all.
- Alt + H, A, F (Windows) to attach a file in the reply window.
- Ctrl + C and Ctrl + V to copy and paste attachments directly into the reply.
These shortcuts don’t change the setting but make manual attachment handling faster.
Frequently Asked Questions
How Do I Keep Attachments When Replying In Outlook 365?
Go to File > Options > Mail. Under Replies and forwards, select “Include original message text” or “Attach original message”. Click OK. This works for Outlook 365 desktop version.
Why Are My Attachments Missing When I Reply In Outlook?
Outlook removes attachments by default to keep replies clean. Change the reply setting in Options > Mail to include original message text. This preserves attachments in future replies.
Can I Keep Attachments When Replying In Outlook Web App?
Yes, but manually. Open the reply, find attachments in the quoted message, and drag them to the top. Or click the paperclip icon to re-upload them. There’s no automatic setting in the web version.
Does The Setting Affect Forwarded Emails Too?
Yes, the same setting applies to forwarded messages. If you change the reply setting, it also affects forwards. Check the dropdown for “When forwarding a message” to adjust separately.
How Do I Remove Attachments From A Reply After Changing The Setting?
After changing the setting, attachments appear automatically. To remove them, click the X next to each attachment in the reply window. This deletes them from that specific reply only.
Final Thoughts On Keeping Attachments In Outlook
Preserving attachments when replying in Outlook is straightforward once you know where to look. The setting is in the Options menu under Mail. Change it to include original message text or attach the original message.
For web users, manual dragging is the only option. Mac users have a similar setting in Preferences. Test your changes to ensure they work.
Remember that this setting applies to all replies and forwards. Use it carefully to avoid sharing files unintentionally. If you only need attachments occasionally, the manual method works fine.
Now you know how to keep attachments when replying in Outlook. No more re-attaching files or losing important context. Your replies will be complete and efficient.
If you run into issues, check the troubleshooting section. Most problems are easy to fix. With this guide, you’re set to handle attachments like a pro.