Guide · checked November 2026
Outlook email templates with attachments: what actually works
Outlook has several template features, and they behave differently in classic Outlook, new Outlook and on the web. Here's which ones keep your files, and a simple setup that works everywhere.
Outlook's built-in options
- My Templates (new Outlook, web, classic): fine for short text, but it can't hold file attachments and only very small images.
- .oft files (classic Outlook for Windows): keep the subject, formatting and attachments, but live as files on one PC. Office Watch describes the older file-based templates as on the way out.
- Mail templates in the cloud (new Outlook and web, Microsoft 365 mailboxes): the newer replacement for .oft. Availability still varies by account type and app, so check it in yours before you rely on it.
- Quick Parts: reusable blocks of text, not whole emails with files.
The common gap: a template that keeps your PDFs and photos and works on every device, without copying it by hand each time.
A setup that works everywhere: a Templates folder
Make a mail folder called “Templates” and keep one finished email per template in it, with the attachments and photos already in place. Type blanks in square brackets wherever details change:
Hi [Client name], here's our proposal for [Company]…
Because it's just a folder in your mailbox, it syncs to classic Outlook, new Outlook, the web and your phone, and works with Outlook.com as well as Microsoft 365.
Let Claude fill it in
On its own, a folder of emails still means copying, editing and re-attaching. Draftbee connects that folder to Claude: you ask for “my proposal email for Sam at Contoso”, and a new draft appears in Outlook with the blanks filled and every file and photo in place. The template email is never changed, and nothing is sent until you press Send.
Set it up in five minutes
- Sign in with Microsoft at app.draftbee.app. Your 14-day free trial starts, no card needed.
- In Claude, go to Settings, then Connectors, then Add custom connector. Paste the link your account page shows.
- Put an email you send often into an Outlook folder called “Templates”, with blanks like [Client name].
- Ask Claude to use that template for someone. The draft appears in Outlook for you to check and send.
Common questions
Can My Templates in new Outlook include attachments?
No. My Templates is meant for short text and can't carry file attachments.
Do .oft templates keep attachments?
Yes, an .oft saved from classic Outlook for Windows keeps its attachments, but it's a file on one computer and the older template formats are being phased out in favour of cloud templates.
Can Claude fill in my Outlook templates?
With Draftbee, yes. Keep the email in an Outlook folder called Templates with blanks like [Client name], and Claude creates a filled draft with the attachments and photos in place.