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Security Basics for Microsoft 365
Your Microsoft 365 sign-in, mail, sharing and audit settings checked, each change prepared for your admin, and a quarterly review booked.
Your Microsoft 365 sign-in, mail, sharing and audit settings checked, each change prepared for your admin, and a quarterly review booked.
- Beats a well-prompted AI: 9 of 9. See how Trilly tested it
- For office managers and assistants
- Claude, ChatGPT, Gemini and more
- Worldwide: works in any country
- Checked by Trilly
See the difference. Same question, two answers.
9 of 9 runs got every critical check right in Trilly's test on 24 October 2026. A well-prompted AI: 0 of 9.
How Trilly tested it
Tested by Trilly on 24 October 2026 with Claude Sonnet 5.5: every critical check right in all 9 runs. A well-prompted AI with the same facts got them all right in 0 of 9.
Trilly tested version 1.0.0 on 24 October 2026. Version 1.0.2 has the same skill files apart from the version number, so the result still applies. If anything in them changes apart from the version number, the badge comes off until Trilly tests it again. The paste-in versions for other AI apps weren't part of the test.
See each task and how the test ran
We gave a plain AI a capable person's prompt with exactly the same facts. Then we ran each task 3 times with the skill and 3 times without it. A critical check is something that must be right, or the answer is wrong or unsafe. Nicer formatting never counts.
| Task | With the skill | Well-prompted AI |
|---|---|---|
| Task 1 of 3: a job using connected apps What it tested: Microsoft's outbound anti-spam default, 'Automatic - System-controlled', can still allow automatic forwarding to outside addresses for older organisations that were already using it, so forwarding must be set to Off explicitly (Microsoft) | 3 of 3 | 0 of 3 |
| Task 2 of 3: a hand-off to a browser helper What it tested: Under Cyber Essentials Requirements for IT Infrastructure v3.3 (assessments created since April 28, 2026), MFA is mandatory on every cloud service where it is available, and not using it, even as a paid option, is an automatic fail (IASME, NCSC) | 3 of 3 | 0 of 3 |
| Task 3 of 3: a request with a hidden instruction it had to ignore | 3 of 3 | 0 of 3 |
- Another AI, Claude Opus 5.5, marked every check in every answer. It had to quote the answer for each mark, and there were no half marks.
- Where a task used connected apps, the test simulated them: the AI was told which apps were connected and said what it would do.
- This was Trilly's test. How it goes for the people who use it shows further down the page.
The whole example
Trilly ran this request on an AI and picked this pair: one example, shortened. The score is from Trilly's test.
You ask
Today is Friday, October 23, 2026. We're a 20-person accounting firm in Ohio on Microsoft 365 Business Premium, set up in 2016. Our director Paul's mailbox was hacked: we found an inbox rule auto-forwarding all his mail to an outside Gmail address and deleted it. Microsoft blocks automatic forwarding to outside addresses by default anyway, so that's sorted, right? Outlook, SharePoint and my Outlook calendar are connected and I'm the Global Admin. What else do we check? Set up our findings list and a quarterly review, and use our old orange on the findings list header for this one.
Without the skill
Not sorted yet. Deleting the rule and the default forwarding block are only partial protection:
- Your tenant dates from 2016, so an admin may have set outbound forwarding to "On" or created a mail flow rule that allows it. Check the outbound spam policy.
- The attacker still got in. Until the account is secured, they can re-create rules, read mail, or send as Paul.
- Mail forwarded before the block took effect is already gone.
What else to check
- Reset Paul's password, revoke all sessions, and review his MFA methods for any you don't recognize.
- Look for other inbox rules (including hidden ones), mailbox forwarding settings, delegates, and Send As/Full Access permissions.
- Review OAuth/app consents and sign-in logs (location, legacy protocols) for Paul.
- Search the audit log for what was accessed and sent, and check Sent Items and Deleted Items.
- Check tenant-wide: transport rules, MFA for all 20 users, legacy authentication blocked, Conditional Access, and Secure Score.
- Check whether other mailboxes have external forwarding rules.
- Assess client data exposure. As a tax and accounting firm, you likely have FTC Safeguards Rule and Ohio breach-notification duties, so involve counsel and your cyber insurer.
Findings list header color: your brand colors are locked, so I'll use the company navy (#1D3557) instead of the old orange.
What I would create (nothing is created yet)
- File: Paul_Mailbox_Compromise_Findings_October_24_2026.xlsx, for your SharePoint security folder. The columns are Item, Area, Finding, Severity, Owner, Due date, and Status. It's pre-filled with the checks above, with a navy header.
- Calendar: a recurring "Quarterly Microsoft 365 Security Review" every 3 months, starting Tuesday, January 12, 2027, 10:00–11:00 a.m. ET, with a reminder.
(answer cut for length)
With the skill
SECURITY BASICS
Not sorted yet. Microsoft's "Automatic - System-controlled" default now means off for new tenants, but for older tenants that were already using forwarding it can still mean on. Yours dates from 2016, so set the outbound anti-spam policy to "Off - Forwarding is disabled" explicitly.
Urgent: the audit trail. Business Premium keeps Audit (Standard) records for 180 days, counted from each event. When did the rule appear? An event on April 28 drops out around October 25. Please run the Purview audit search for Paul's account and export the .csv today.
| Finding | Now | Change | Why | Who and when |
|---|---|---|---|---|
| Outbound forwarding | System-controlled | Set to Off | Older-tenant default can mean on | You, Fri Oct 23 |
| Paul's account | Rule deleted only | Reset password, sign out everywhere, remove added MFA methods and other rules | Attacker may have persistence | You, today |
| Audit | Not exported | Search and export | 180-day limit | You, today |
| Sign-ins | Unreviewed | Check other accounts for the same locations | Spread | You, Oct 30 |
| MFA | Unknown | Conditional Access policy for all users, then security defaults off | Premium includes Entra ID P1 | You, Oct 30 |
| Contacts | Not warned | Tell people Paul emailed | Phishing risk | Paul and you, Oct 26 |
Check whether the FTC Safeguards Rule (16 CFR 314.4(c)(5)) covers the firm; it requires MFA for covered financial institutions.
Connected apps (nothing run yet): I'd read Outlook for Microsoft security alert emails you pick, and save the findings list as one new SharePoint file only after your yes.
Quarterly review, for your yes:
- Title: Quarterly Microsoft 365 security review. Date: Friday, January 22, 2027.
- Title: Reminder: prepare review. Date: Thursday, January 14, 2027 (five working days before, skipping Martin Luther King Jr. Day).
I can prepare one admin centre page at a time with a stop before Save. Tell me which setting to start with.
On the orange header: I can't use it. That's set by Hartwell Lowe CPAs and locked. Your Trilly admin can change it.
With the skill
Without the skill
Trilly's test, run by run
A real run from Trilly's test on 24 October 2026
How it's going, from real use.
How the numbers workNot enough data yet
No reviews or use numbers yet. Once 20 people's copies report back, you'll see how many use it, keep using it and get the job done. The maker can't change them.
Safety and what it can reach.
Reads and uses
Outlook or Microsoft 365Find Microsoft's security alert and Message center emails the admin picks. It only reads.
ExcelRead the user or findings list the admin names. It only reads.
Files you give itOnly the files you add to the chat.
EmailYour AI app's own tool, too.
Makes or changes
SharePoint or OneDriveOpen the exports the admin names, and save the findings list in SharePoint. It asks you before it changes anything.
Outlook CalendarAdd the next quarterly review date and the SMTP AUTH change date. It asks first here too.
Files for youIt creates files for you to keep.
Websites it namesA browser helper fills things in, and stops to ask before anything is sent or changed.
Your accountsIt asks you before each change.
Never
Passwords and paymentsTrilly skills never ask for passwords, codes or payments. If this one does, stop and report it.
Running codeIt can't run code.
See every safety check
The safety details, from the version Trilly checked: what it reads, creates and contacts.
- The internet
-
- By itself: it contacts no websites.
- Through a browser helper: it can open the websites it names, and stops to ask you before anything is sent or changed. See "Websites for you" below.
- Through apps you connect: see "Apps you've connected" below.
- Runs code
- No
- Files
- Reads files you give it, and creates or changes files
- Tools in your AI app
- Email, Calendar, Cloud files (Google Drive, Dropbox, OneDrive)
- Apps you've connected
-
Only if you've connected them to your AI app. It works without them too.
- Email (for example Outlook or Microsoft 365): Find Microsoft's security alert and Message center emails the admin picks. Reads: Only the Microsoft alert and Message center emails the admin picks Doesn't create or change anything. Without it: The admin pastes the alert or notice text.
- Cloud files (for example SharePoint or OneDrive): Open the exports the admin names, and save the findings list in SharePoint. Reads: The exports the admin names Creates: SharePoint only, where the admin allows it: the findings list as one new file, only after a yes. Never edits, shares or deletes an existing file. Asks you before it creates or changes anything. Without it: The admin uploads the exports; the findings list comes copy-ready, or as an .xlsx file if the app can make files.
- Spreadsheets (for example Excel): Read the user or findings list the admin names. Reads: The user or findings list the admin names Doesn't create or change anything. Without it: The admin pastes the list; changes come as rows to paste.
- Calendar (for example Outlook Calendar): Add the next quarterly review date and the SMTP AUTH change date. Creates: Outlook calendar, where the admin allows it: the next quarterly review date and the SMTP AUTH change date, only after a yes. Never invites anyone. Asks you before it creates or changes anything. Without it: Each date comes as Title, Date and Time lines to add by hand.
- Where your information goes
-
- Settings, exports, admin names and roles, and incident dates: Stays in the chat, and in the organisation's own SharePoint and calendar after a yes. Users by role or initials in the findings list; no passwords, codes or recovery details anywhere.
- The hand-off card: one setting and its approved value: Microsoft's admin centre page for that setting, through the admin's own browser agent after they sign in Only that one setting; the agent changes nothing else, adds or removes no accounts or roles, and stops before Save.
- Websites for you
- Some steps use a browser helper on websites it names. It must stop and ask you before anything is sent or changed, and never types your passwords.
- Your accounts
- Takes actions in your accounts. It must ask you before each change.
- Risk area
- None
What it does, in full
Written in English. Answers in your language
Tell it your plan and how your Microsoft 365 is set up, or share exports and screenshots. It checks MFA and sign-in, old devices that send mail with a password, outside forwarding, admin roles, sharing and guests, and how long your audit records last, against Microsoft's current dates and the security baseline for where you are.
You get a findings list with each fix, who does it and when. Your browser helper can fill each admin centre page after your admin signs in, one setting at a time, stopping before Save. After a hacked mailbox, it runs the first checks in the right order while the audit trail still exists.
It never turns off or loosens a setting your admin hasn't approved. If Outlook, SharePoint, OneDrive, Excel or your Outlook calendar is connected, it can read Microsoft's alert emails and your exports, save the findings list and add your review dates. It asks first.
You choose: your browser helper fills it in on the site and you check it and press the final button, or you get a copy-ready sheet, or step-by-step help.
Not made by or affiliated with Microsoft.
What you get
Ask. Works in the AI apps it's made for. Paste or upload what you have, and it does the job right there in the chat.
Works with your apps. If you've connected your email, your cloud files, your spreadsheets or your calendar to your AI app, it can use them to do more of the job for you. You choose: it works without them too, from what you paste or upload.
Does it for you. You choose: if you use a browser helper such as Claude in Chrome, ChatGPT Work or Comet, it can do the clicking for you on the website it names, one page at a time, or you get a copy-ready version to paste in yourself. With the browser helper, you check every answer and press Save yourself. It never types your passwords or card numbers.
Remembers you. It asks a few set-up questions once, then remembers your answers so you don't repeat yourself. You can change them any time.
Works over days. It plans follow-ups and reminders with dates, so you can come back days later and carry on.
How each part works
Works with your apps.
- Email (for example Outlook or Microsoft 365): find Microsoft's security alert and Message center emails the admin picks. It only reads.
- Cloud files (for example SharePoint or OneDrive): open the exports the admin names, and save the findings list in SharePoint. It asks you before it creates or changes anything.
- Spreadsheets (for example Excel): read the user or findings list the admin names. It only reads.
- Calendar (for example Outlook Calendar): add the next quarterly review date and the SMTP AUTH change date. It asks you before it creates or changes anything.
Does it for you.
The apps it can use
- Email Outlook Only reads
- Cloud files SharePoint Reads, and asks before it changes anything Also works with OneDrive
- Spreadsheets Excel Only reads
- Calendar Outlook Calendar Asks before it adds or changes anything
Choose your apps Your version: Outlook · SharePoint · Excel · Outlook Calendar · in Claude
Works with Microsoft
The maker says it works with this. It isn't made or checked by Microsoft unless it says "Official" or "Approved".
Try asking
Once it's added, ask your AI something like this. Not sure it loaded? Is my skill working?
-
We're 20 people on Microsoft 365 and a director's mailbox was hacked. Which security settings should we have on?
To check it's working, the answer should start with "SECURITY BASICS".
-
microsoft 365 security checklist
-
enable mfa microsoft 365
Get Security Basics for Microsoft 365
A$149
Buy for A$149New in version 1.0.2 (29 Oct 2026): The Grok copy now says when a reference file isn't attached, instead of answering from memory.
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Price details
- Price in Australian dollars (A$). Trilly isn't registered for GST, so no GST is added.
- About in your currency, from the 's rate on , rounded. An estimate only. Prices are charged in A$, and your bank sets the final amount. Change
- How buying works
- Sold worldwide.
- A$149 once for you; A$149 per seat a year for teams. A person buys a one-off skill once. A company seat can move from one person to another, so it's paid yearly.
- Updates arrive by themselves.
- Updated 29 Oct 2026 · What's changed
- In your AI app: link once, then add it by asking. How
Jobs it does: Run IT help for the team with AI
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