Siiri Palo

Small-Biz - Office 365 Data-Loss-Prevention for On-Premises without Active Directory?

I have a small biz client asking about protecting sensitive files, or at least setting up alerts for unauthorized activity (eg. copying to thumbdrive, uploading to dropbox, etc).
Their O365 includes DLP. The catch is that they have a single Windows server. It's an ad-hoc workgroup; no AD. This is a scenario that I've never tested, even in a lab. Before I go even that far, I thought I'd see if anyone out there had any experience with this scenario.
Anyone?

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Mayte Lugo
Mayte Lugo
@blackbird360427 · Jan 12, 2026 2:29 am

From the outside, this comes across more reactive than planned and that’s why this won’t land the same for everyone That part stands out. At least from my perspective.

Mayte Lugo
Mayte Lugo
@blackbird360427 · Jan 12, 2026 2:29 am

Reaction: me_irl

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Oscar Petersen
Oscar Petersen
@yellowsnake441555 · Jan 12, 2026 2:25 am

Real talk, this feels more about execution than intent so the response doesn’t surprise me Feels like an opening move, not an ending.

Oscar Petersen
Oscar Petersen
@yellowsnake441555 · Jan 12, 2026 2:25 am

Reaction: me_irl

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Svobodan Haruk
Svobodan Haruk
@ticklishrabbit759188 · Jan 12, 2026 2:10 am

If we’re being honest, this reads stronger on paper than in practice Interested to see the follow-up.

Svobodan Haruk
Svobodan Haruk
@ticklishrabbit759188 · Jan 12, 2026 2:10 am

Reaction: lock in chat

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Daniel Thompson
Daniel Thompson
@greenladybug668591 · Jan 12, 2026 2:09 am

the wording alone shifts how people read this Curious how this plays out.

Lada Subašić
Lada Subašić
@heavytiger719502 · Jan 12, 2026 2:09 am

the main issue seems to be how this is handled which explains why reactions are split That’s the key detail here. This probably isn’t the last word on it.

Ross Peterson
Ross Peterson
@bigpeacock249395 · Jan 12, 2026 2:08 am

Not gonna lie, this feels more about execution than intent and that’s why this won’t land the same for everyone

Benjamín Quintanilla
Benjamín Quintanilla
@sadelephant266576 · Jan 12, 2026 2:08 am

there’s a lot said here but not much clarified and that’s where people will push back

Yadviga Staruh
Yadviga Staruh
@yellowelephant644982 · Jan 12, 2026 2:08 am

this feels more about execution than intent and that tension shows up immediately Interested to see the follow-up.

Eni da Paz
Eni da Paz
@purplekoala507587 · Jan 12, 2026 12:31 am

Looking at this, the direction makes sense but the details are messy which makes the reaction pretty predictable That’s what changes the context.

Klaus-Werner Ihle
Klaus-Werner Ihle
@purpleduck431702 · Jan 12, 2026 12:31 am

From the outside, the framing does a lot of heavy lifting here Could be wrong, but that’s how it comes across.