Unable to save complete email to File Explorer or as attachement to another email

Question

Unable to save complete email to File Explorer or as attachement to another email

Benni 0

For years, I have used 'drag and drop' to move emails from Outlook to File Explorer, or to attach to other emails. These processes are not working and result in incomplete email histories.

For filing: I simply selected the latest email (which contained the entire correspondence history and all attachments) and used a right mouse click to drag and 'move' the email to the relevant File Explorer folder. This created a stand alone .msg file (or 'blob' of information) that could be attached to other emails, or double clicked to open and start an email trail again. This was fast and efficient. This method no longer works properly. It is only saving the header and text from the very last email ie - the entire history is lost. I have also tried 'save as' when the email is open, but it results in the same outcome.

For attachments: I also checked an email that had another email as an attachment and the attachment was corrupted ie - it only showed the mail header and no text in the body. My workflow is to attach email receipts to the order email to have a complete record of the transaction. In this case I had received 2 individual emails that were normal, opened 1 email and selected forward, and then dragged the other email onto it as an attachment.

I am using Windows 11, Classic Outlook and Microsoft 365 with a local account.

Does anyone know the what has caused this issue and the fix? TIA

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2 answers

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Answer 1

Hi

thanks for your response.

No, I don't use conversations. When I select and open a single email in the Outlook client using double click, it shows the entire text history. In this case, it was a communication between 2 people only and has several replies back and forth with all attachments showing.

My account is set up as IMAP.

Please note that I use Office via Parallels on a Mac, and recently had to create a new Virtual Machine. I've only have these problems since then so it's possible some configuration in Windows/Office has changed.

I have re-posted here as this was deleted when entered as a comment. Sorry.

Answer 2

Francisco Montilla 31,535 Independent Advisor

Hello

Since we need to pinpoint exactly what is happening here before testing a fix, let's gather a bit more info to make sure we are on the right track.

When you mention selecting the latest email and expecting it to carry the entire history and attachments, I am curious if your inbox is currently grouping messages by conversation. When an inbox visually rolls up replies into a single thread, clicking and dragging that top line into File Explorer or another message will often only grab that one last reply instead of bundling the entire history. Have you recently changed your view settings to show as conversations?

If you just double click to open that last email by itself in a new window without moving it, does its body physically hold all the old quoted text and older attachments you were expecting to see?

You also mentioned that dragging a normal email into another one as an attachment caused it to lose its body text entirely. Can you clarify how your email account is set up in Classic Outlook, like whether it is an IMAP or Exchange connection?

Let me know those details and we can figure this out.

Benni 0 Reputation points

2026-10-12T06:17:28.6466667+00:00

Hi

thanks for your response.

No, I don't use conversations. When I select and open a single email in the Outlook client using double click, it shows the entire text history. In this case, it was a communication between 2 people only and has several replies back and forth with all attachments showing.

My account is set up as IMAP.

Please note that I use Office via Parallels on a Mac, and recently had to create a new Virtual Machine. I've only have these problems since then so it's possible some configuration in Windows/Office has changed.
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Francisco Montilla 31,535 Reputation points Independent Advisor

2026-10-13T03:57:40.14+00:00

That detail about the brand new VM and IMAP explains the behavior.

When you set up an IMAP account from scratch in Classic Outlook, it frequently defaults to downloading headers only rather than saving the full message bodies and attachments into your local data file. When you double click an email inside Outlook, it streams the content live from the server into your viewing window, but when you drag it into File Explorer or attach it to another email, Outlook pulls directly from that local offline cache. If the local cache only holds the header, the exported file or attachment ends up stripped of its body text and history.

To fix this, you just need to tell Outlook to keep complete copies of your IMAP messages locally.

Press Ctrl + Alt + S on your keyboard to open the Send/Receive Groups menu. Make sure All Accounts is selected, then click the Edit button on the right. In the left column, click on your IMAP account and make sure the box to "include the account in this group" is checked. In the folder tree, select your Inbox, then look down at the Folder Options at the bottom and switch the radio button to Download complete items including attachments. You can do the same for your Sent Items or any other folders you regularly archive from, then click OK and hit Close.

Once you are back in the main Outlook window, press F9 to start a full send and receive so Outlook can pull down the missing message bodies. When the status bar at the bottom finishes syncing, test it by dragging an email into a folder or attaching it to a draft, then open that saved file to verify that the full conversation history and attachments are intact.
Benni 0 Reputation points

2026-10-14T04:37:16.33+00:00

Thanks for such a detailed explanation. I have checked these settings and all my accounts are already set to 'Download complete items including attachments'. I wasn't sure if I should clear the setting, close Outlook and then re-open it and reset the setting (I did not try this).

Interestingly the Folder Options screen is slightly different for Outlook.com accounts and non Outlook.com accounts (I also use a number of iCloud accounts). With the Outlook account, the check boxes for every folder in Folder Options are enabled; whereas the iCloud accounts, everything under Folder Options is greyed out. However, the option Download complete items including attachments is still available in the section Account Options under Receive Mail Items (and is checked).

I also did a quick test saving my emails as different file types. Ordinarily I want to use .msg to preserve all the email details, with the attachments, but I wanted to test current behaviour. I have 'rich text' and 'html' email types in my inbox; in both cases if I choose 'save as' text, or save as html, to File Explorer, the entire message history was saved (without attachments).

I don't understand how some of the information is available and saved for certain file types but not others.
Francisco Montilla 31,535 Reputation points Independent Advisor

2026-10-14T04:47:07.85+00:00
First, to clear up why those two things you noticed are happening, the greyed out Folder Options list on your iCloud accounts is actually normal. When the top section under Receive Mail Items is set to download complete items for subscribed folders, Outlook locks the individual folder list below it and applies the rule across the board.

As for why Text and HTML files keep the full history while .msg files do not, it comes down to how Outlook builds those files. When an email is open on your screen and you save it as Text or HTML, Outlook simply scrapes the visible text currently rendered in your viewing window and writes it into a flat file. When you save as .msg or drag and drop an email, Outlook does not grab what is on your screen. Instead, it packages the raw underlying MAPI database properties directly from your local data file into a structured container. If something interferes with how those raw properties are stored or translated, the .msg output ends up blank or cut off even though the email looks totally fine on screen.

Since this started right after moving to the new Parallels VM and we know your sync settings are already correct, I want to narrow down what is corrupting that .msg packaging before we start changing settings.

Does this problem happen when you drag or save emails from your Outlook.com account too, or is it only happening with emails inside your iCloud accounts?

Also, on those back and forth emails where only the very last reply gets saved, does that last reply happen to have an attachment or an inline image like a signature logo right where the rest of the history cuts off?

Finally, did you install the iCloud for Windows app inside this new VM to sync your mail, or did you just add the iCloud addresses manually into Outlook using app passwords?

Let me know what you see on those three points and we will go from there.
Benni 0 Reputation points

2026-10-16T05:08:41.8533333+00:00
Ok - I understand your responses to my 2 questions. Re your questions:

I primarily use my iCloud accounts. To test Outlook.com, I forwarded an existing email from my iCloud account and tried to save it using both Drag and Drop and File Save As. Both failed with only part email saved.

Yes, the back and forth email does have images at the cut off point. I tested some of other emails that had graphics; some saved OK and some cut-off at the line of images so I'm unclear what the commonality is.

I've never used iCloud for Windows hence just added the iCloud accounts manually using app passwords. This was the same method I used in the previous VM.
Francisco Montilla 31,535 Reputation points Independent Advisor

2026-10-16T13:08:18.54+00:00

Okay. Since the cutoff is happening right at the line where an image appears across both accounts, it is almost certainly an Outlook setting that controls how Word re-encodes message graphics when it builds a file or an attachment.

Please try this: In Outlook, click on File in the top left corner and select Options. Click on Mail in the left menu, then scroll down until you reach the Message format section. Find the setting that says Reduce message size by removing format information not necessary to display the message. If that box is checked, uncheck it. Click OK at the bottom to save the change, then close Outlook completely and restart it.

Once Outlook reopens, try dragging that same back-and-forth email to File Explorer or attaching it to a draft again. Open the resulting message file to see if the full history and attachments carry over past the image.
Benni 0 Reputation points

2026-10-17T04:01:19.82+00:00

The box was checked so I unchecked it, restarted Outlook and tried saving the email. Both Drag and Drop and File Save As failed.
Francisco Montilla 31,535 Reputation points Independent Advisor

2026-10-17T11:17:40.05+00:00

I see. Looks like the issue is tied directly to how Outlook is handling external graphics.

Try this now please. In Outlook, click on File in the top left corner and select Options. Click on Trust Center on the left side, then click the Trust Center Settings button on the right. Click on Automatic Download on the left side of the new window. Uncheck the top box that says Don't download pictures automatically in standard HTML email messages or RSS items. Click OK, then click OK again to save the changes, and restart Outlook.

Open that problematic email, make sure all the images and graphics load up fully in the window, and then try saving it as a .msg file or dragging it into File Explorer again.