New Outlook · Sent-mail rules

"Apply rule on messages I send" is gone from New Outlook. Here's what happened — and how to get it back.

By John Johnson, retired network architect · Updated September 18, 2026

For two decades, classic Outlook had a quiet power feature: when you created a rule, you could choose "Apply rule on messages I send." Mail you sent to a client filed itself into that client's folder. Sent and received mail for a project lived together. Your Sent Items folder stayed clean without you touching it.

New Outlook for Windows, Outlook on the web, and Outlook mobile removed it. Their rules engine fires only on mail you receive. There is no setting to find, no toggle you're missing — rules for sent messages simply do not exist in New Outlook. Threads asking for it back have collected dozens of "I have this question too" votes on Microsoft's own forums, and the official answer, year after year, has been a link to the feedback portal.

What exactly was removed

In classic Outlook (the desktop program many businesses still run), the Rules Wizard offers two starting points: rules that check messages when they arrive, and rules that check messages after sending. That second path is the one that never made the jump. In New Outlook, Settings → Mail → Rules builds incoming-mail rules only. Anything you send lands in Sent Items and stays there until a human drags it somewhere.

If you keep a folder per client, per project, or per matter — the filing style of consultants, lawyers, real-estate agents, executive assistants, and anyone who answers to "where's that email you sent them?" — this removal broke your workflow.

The free workaround: BCC yourself

There is one native workaround, and in fairness it works. Here it is in full, so you can decide if it's enough:

1. BCC yourself on every message you want filed. (Add your own address in the BCC field before you hit Send.)
2. In New Outlook, go to Settings → Mail → Rules → Add new rule.
3. Condition: To (or From) contains your own address — the BCC copy arrives addressed from you.
4. Add a second condition if you want per-client filing (for example, subject or recipient keywords).
5. Action: Move to the folder you want.

The costs, stated plainly: the filed message is an unread duplicate, not the true item from Sent Items, so your folder holds a copy addressed to yourself while the original still sits in Sent Items. You must remember the BCC on every single message, from every device. And per-client filing means one rule per client with conditions that guess at the right mail. Many people run this for a while and go back to dragging.

The real fix: put the rule back

I'm a retired network architect. I filed sent mail by rule for twenty years, and after enough months of waiting for Microsoft I built the missing piece myself. Founder disclosure, plainly: what follows describes my own product, and the free workaround above is complete on purpose — if it covers your needs, use it and keep your money.

SentRules restores "apply rule on messages I send" as a service that works with New Outlook instead of against it:

• You write a rule once — "anything I send to acme.com goes to Clients/Acme."
• You keep Outlook's normal Send button. Nothing to install, no add-in, no toolbar.
• SentRules waits for the confirmed sent copy Outlook already creates, then moves it to the right folder — the real sent item, not a duplicate.
• It works no matter where you sent from: New Outlook, classic, the web, your phone.
• It never sends mail on your behalf — it never even asks for that permission — and it refuses to file anything into Deleted Items or Junk. When in doubt, it leaves mail alone.

	Do nothing	BCC yourself (free)	SentRules
Sent mail filed automatically	No	Copy only	Yes — the real sent item
Works from phone	—	If you remember the BCC	Yes, automatically
Effort per email	Drag by hand	Remember the BCC	None
Cost	Your time	Free	$4.99/mo or $39.99/yr, 14-day free trial

Frequently asked questions

Why can't I apply a rule to messages I send in New Outlook?

Because New Outlook's rules engine only processes incoming mail. The classic "Apply rule on messages I send" option wasn't carried over, and Microsoft's official guidance is to vote for the feature on the feedback portal.

Is there any setting that turns sent-mail rules on?

No. This isn't a hidden toggle — the capability doesn't exist in New Outlook, Outlook on the web, or Outlook mobile.

Will Microsoft bring it back?

No date has been announced. The feedback-portal request has been open for years.

Does the BCC workaround file the real sent message?

No — it files an unread copy addressed to you. The original stays in Sent Items.

Does SentRules work with personal outlook.com accounts?

Yes — personal outlook.com, hotmail and live accounts, and Microsoft 365 work accounts.

Is SentRules affiliated with Microsoft?

No. SentRules is an independent service and is not affiliated with or endorsed by Microsoft.

Want the complete menu of options — including staying on classic Outlook and Power Automate — with the honest costs of each? See the full guide: Rules for sent emails in New Outlook: every option that works.