Outlook’s calendar quietly gets useful, Teams quality-of-life fixes land, Copilot brings Claude into Word, Excel, and PowerPoint, and what July’s price rise means for you.
May is a quieter month than April, but in many ways a more useful one. Outlook has gained a handful of small features that, taken together, make the inbox and calendar genuinely faster to live in. Teams has tightened up the meeting experience, especially around joining, focus, and notifications. And Copilot has had its biggest behind-the-scenes change in years, with Anthropic’s Claude models now available alongside OpenAI inside Word, Excel, and PowerPoint.
At the same time, the July 2026 price increases are now only weeks away, and Microsoft has confirmed the final numbers. If your renewal is anywhere near 1 July, it is worth pausing to check before then.
This month focuses on Outlook as your team’s quiet command centre, a closer look at the new Copilot model picker, and a short health check on your inbox and calendar habits.
As always, the aim is not more tools. It is calmer, clearer day-to-day work.
If you only read one section, read this.
App: Outlook | Status: Rolling out (web first, desktop following)
Your peers, direct reports, and manager now appear automatically under People’s calendars in the Outlook calendar navigation pane. Click any one of them and their calendar overlays onto your own, so you can see free slots without asking around or opening a Scheduling Assistant. The list is built from your reporting line and the people you meet with most, so it stays relevant without manual setup.
What this means for you: Quicker scheduling, fewer ‘when are you free’ messages in chat.
App: Outlook (new Outlook and web) | Status: Available now
The new Outlook now lets you sort the message list by flag status, due date, or start date. Combined with categories, this turns the inbox into a lightweight follow-up list that you actually keep on top of. Flagged items behave like a to-do list synced with email, so the things you have promised to come back to surface to the top instead of drifting down the inbox.
What this means for you: Your flagged emails finally behave like a real to-do list.
App: Teams | Status: Rolling out through May
Before you hit Join, Teams now runs a quick mic, camera, and speaker check so the first three minutes of every meeting are not lost to troubleshooting. The check runs in the join screen automatically and flags anything that looks wrong, with a one-click fix for the most common problems. It is particularly useful before client calls or interviews when you cannot afford to fumble.
What this means for you: Fewer ‘can you hear me now?’ moments at the top of every call.
App: Teams on Windows | Status: Available now
Turn on Focus in Windows 11 and Teams will now match automatically, silencing pings during deep work. Previously you had to remember to set Do Not Disturb in two places. Now one switch covers both, so a focus block in your calendar can genuinely mean uninterrupted time.
What this means for you: One switch silences both apps for deep work.
Copilot Adds a Model Picker With Claude
App: Word, Excel, PowerPoint | Status: Rolling out through May
Microsoft has added Anthropic’s Claude models alongside OpenAI inside the apps you already use. Open the Copilot side panel and you will see a small model selector at the top. The default still works the way it always has, but you can now pick Claude for tasks where a different style helps, such as long-form writing, careful summarisation, or structured analysis. This is the biggest behind-the-scenes change to Copilot since launch.
What this means for you: A genuine second opinion when one model gets stuck on a draft.
App: Outlook on iOS and Android | Status: Rolling out
You can now propose new times for meeting invites, tentatively accept invitations, and use shared mailboxes directly from your phone. Together with the existing Follow a Meeting button, this means most of what you used to need a laptop for can now be done on mobile.
What this means for you: Less time waiting until you are back at your desk to clear small actions.
App: Teams | Status: Available now
Raising your hand or sending a quick reaction no longer requires opening a menu. The most common reactions sit on the meeting toolbar permanently, and Raise Hand is a single click. Meeting moderators can also see the order in which hands went up, so questions are taken fairly.
What this means for you: Smoother participation in large meetings, especially for quieter voices.
App: Teams | Status: Rolling out through May
Live transcription can now be turned on without also starting a recording. The transcript appears live during the meeting and is saved afterwards, but no video file is produced. Useful for sensitive conversations where you want a written record but not a recording on the system.
What this means for you: Take notes automatically without the awkwardness of recording the room.
App: Outlook on the web | Status: Rolling out
If you need to share a meeting with someone outside your organisation, or who is not on Microsoft 365, you can now save the event as a standard .ics calendar file. Send it by email, drop it in a chat, or upload it to a portal. The recipient can add it to any calendar app.
What this means for you: Easier to coordinate with clients, contractors, or anyone outside your tenant.
App: Teams | Status: Rolling out late May, on by default
When someone calls you on Teams pretending to be a familiar brand, the call screen will now show a clear warning before you answer. Teams checks the caller against known brand identities and flags any mismatch, so you have a chance to hang up before the conversation starts. This is one of the most useful anti-fraud features Microsoft has shipped in months.
What this means for you: An early heads-up when a caller is not who they appear to be.
App: Outlook on the web and new Outlook | Status: Available now
You can now Ctrl-click in the mini-month picker to view several non-consecutive dates side by side, for example every Friday this month or the days you are due in the office. Previously you could only select a continuous range.
What this means for you: Easier to spot patterns across a fragmented diary.
App: Teams | Status: Available now
Muted chats and meeting chats now live in their own buckets, and a new eye icon toggles read or unread instantly. The unread badge means something useful again, so you can trust it to tell you what genuinely needs attention.
What this means for you: Less visual noise and faster triage of what really needs a reply.
Goal: See every email you flagged, due first.
Steps:
If you don’t see it: You may still be on classic Outlook. Use the toggle at the top right to switch over.
Goal: Check a colleague’s availability without opening a separate window.
Steps:
If you don’t see it: This rolled out across April and May. Restart Outlook if it still does not appear.
Goal: One Focus switch silences both apps at once.
Steps:
If you don’t see it: Your Teams app may need an update. Close and reopen it.
Goal: Compare two AI drafts side by side and pick the one that fits.
Steps:
If you don’t see it: The model picker is rolling out gradually through May. If it is missing, try again in about a week.
Goal: Get a written record of a sensitive conversation without producing a video file.
Steps:
If you don’t see it: This is rolling out through May. If you only see the combined recording and transcription option, your organisation has not had the update yet.
What It Is
Microsoft Outlook is the email and calendar hub of Microsoft 365. The new Outlook on Windows now matches Outlook on the web feature for feature, with a faster interface, smarter search, and Copilot built in. It also runs on Mac, iOS, and Android, with a near-identical experience across all of them.
Why It Matters More Than Most People Realise
Email and calendar are where small teams quietly lose hours every week. The wrong setup turns the inbox into a constant interruption. The right setup turns it into a place where work actually moves. Most SMEs have Outlook already and use perhaps a tenth of what it can do. The features added in April and May are particularly focused on visibility, your flagged items, your team’s calendars, the next available slot, so you spend less time digging and more time deciding.
How SMEs Should Actually Use Outlook
Triage faster with rules and Quick Steps. Right-click any email and choose Create rule to file newsletters, supplier confirmations, or internal CCs into folders automatically. Add a Quick Step for the moves you make daily, for example File and mark read, or Forward to accounts, and your morning sweep becomes one click each. This is the single biggest time saver in Outlook and almost nobody uses it properly.
See your team without leaving Outlook. With the new teammates’ calendars feature, your manager, peers, and direct reports show up in the calendar navigation. Overlay any two together to find a slot in seconds. No more screenshotting a Teams calendar and pasting it into chat, and no more guessing who is in the office today.
Plan the week from your flags. Use Sort by Flag to pull every follow-up to the top of your inbox, then drag flagged items into a calendar block to give them protected time. Flags now behave like a lightweight to-do list synced with email, so nothing important slips off the bottom of the list.
Use categories like a quiet labelling system. Categories are colours you can assign to emails and meetings, and they survive across folders. Use a single colour for a project, a client, or anything you want to find later. Combined with search, this turns Outlook into a personal CRM you do not have to maintain.
What Is Changing This Month
Outlook this month adds automapping of shared calendars between classic and new Outlook, multi-select calendar groups, non-consecutive date selection, sort-by-flag, save-as-ics for external sharing, and full mobile parity for proposing new times and using shared mailboxes. Taken individually each is small. Taken together they make the new Outlook the first version that genuinely feels faster to live in than the classic one.
Common Outlook Mistakes We Still See
Try This Quick Check (2 Minutes)
If any of those gave you pause, it is worth spending fifteen minutes tidying up. A clean Outlook saves everyone time, including yours.
Pro Tip
Use Quick Steps (top of the ribbon on the Home tab) to chain three actions into one button: mark read, file to folder, and forward. It reclaims the most repetitive minute of your day, and it is the single feature most likely to make you smile the first time you use it.
One-Minute Microsoft 365 Win: Outlook Quick Steps
Quick Steps in Outlook let you build a one-click button that runs several actions in sequence. The most popular setup is a button that moves the email to a folder, marks it read, and dismisses it from the inbox, all at once. Once you have built one, the morning sweep through your inbox becomes a series of single clicks instead of three-click loops.
Try it: On the Home tab in Outlook, find Quick Steps in the ribbon, click Create New, name it, then add the actions you want chained together. Right-click any email to run it.
Works on Windows and Mac. Mobile uses Swipe Actions for a simpler version of the same idea.
Copilot Corner: Prompts to Copy
If your organisation has Microsoft 365 Copilot, try these prompts:
Basic prompts to try
SME-focused prompts
One quiet tip: the Anthropic Claude model is particularly good at careful summaries of long threads. If your normal prompt feels rushed or shallow, try switching the model and running it again.
Quick Tip
Right-click any email in Outlook and choose Create rule to file similar messages automatically from now on. It takes about ten seconds and saves the same ten seconds every day after. Over a year, that is roughly an hour of your life back from the newsletter list.
Security Essentials: Caller and Sender Trust
This month’s theme: trust the sender, not the message. Caller and sender impersonation is the dominant phishing pattern this quarter.
Take the new Teams caller warnings seriously. Brand impersonation alerts on VoIP calls are rolling out across May. If you see one, treat the caller as untrusted until you have verified them another way, such as ringing back on a number you already had on file. Example: a ‘Microsoft Support’ call that triggers the warning is almost certainly a scam.
Hover before you click external SharePoint links. A shared file from a familiar name but an unfamiliar tenant is the most common phishing pattern we still see in May 2026. The display name will look right. The domain will not. Hover the link before you click to see the real destination.
Never approve a payment by email alone. If a supplier emails new bank details, ring them on a number you already had on file, not the one in the signature. Example: invoice fraud almost always starts with an email that looks like it came from someone you know.
Use number matching in Authenticator. When the app asks you to type the two-digit number on screen, that is your defence against accidental approvals. If a sign-in prompt arrives without you signing in, do not approve it, and tell your IT contact straight away.
Report phishing with the Report button, not Forward. Forwarding strips the headers your IT team needs to track where the message came from. The Report button in Outlook keeps them intact and sends the message to the right people.
Pause on unknown Teams chat invites. A ‘Hi from accounts’ message from someone you do not recognise is worth pausing on, especially if there is a link or a file. Treat unsolicited Teams chats with the same care as unsolicited emails.
Keep Outlook and Teams mobile apps current. May’s mobile updates patch two issues with shared link previews. Check the App Store or Play Store this week and update both.
The simple rule: verify the sender through a second channel before you act on anything that asks for money, credentials, or unusual access.
AI Meeting Recap Without a Transcript (June 2026)
Teams Premium and Copilot users will get AI-generated meeting recaps even when transcription was off. Useful for sensitive meetings where you do not want a verbatim record but still want decisions and action items captured. Recaps will appear in the meeting chat after the call with a new AI recap badge to make it clear that no transcript was kept. Worth knowing about if you have ever turned off recording because the conversation was sensitive.
Smarter Sharing of Meeting Recaps (June 2026)
Sharing a meeting recap with someone who was not in the room is currently clunky. From June, Teams will let you send a recap as a clean, read-only summary that does not require the recipient to open the full meeting in Teams. Useful when you want to bring a colleague up to speed without making them watch a video.
Cross-Tenant Message Recall in Outlook (August 2026)
Planned for August, this finally lets you recall an email sent to someone outside your company, as long as both organisations run Microsoft 365. Today, recall works only within your own organisation. The standard Recall this message option will simply start working on more emails. Treat it as a safety net for the occasional mistake, not a habit.
Microsoft 365 Commercial Price Increases (1 July 2026)
Now only weeks away. See the pricing section below. If your renewal lands in the second half of the year, check the timing now, not in late June.
Quick Health Check for Owners: Inbox and Calendar Hygiene
Your team lives in Outlook every day. But when was the last time anyone checked whether it is helping or hurting? Five quick questions to sense-check.
The simple rule: an inbox is not a to-do list, and a calendar is not a record of the past. Both work best when they are clean, current, and trusted.
If any of those questions made you uncomfortable, reply and we will help you tidy it up.
Important: Microsoft 365 Price Increases from 1 July 2026
Microsoft has confirmed global pricing increases taking effect from 1 July 2026. These apply to new subscriptions and renewals from that date.
| Plan | Current | From July | Change |
| M365 Business Basic | $6.00 | $7.00 | +17% |
| M365 Business Standard | $12.50 | $14.00 | +12% |
| M365 Business Premium | $22.00 | $22.00 | No change |
| M365 Apps for Business | $8.25 | $10.00 | +21% |
| M365 E3 | $36.00 | $39.00 | +8% |
| M365 E5 | $57.00 | $60.00 | +5% |
| M365 F1 (Frontline) | $2.25 | $3.00 | +33% |
What to do: if your renewal is coming up, renewing before 30 June locks in current pricing for the full term. Review your licences now. If you have unused seats, or people on plans with features they do not use, this is a good time to right-size. UK pricing will mirror these percentage increases (GBP figures not yet confirmed by Microsoft).
If you would like help reviewing your licences before July, get in touch. Five minutes could save a meaningful amount.
We make enterprise-grade IT simple and human for SMEs. We start by maximising the tools you already have, then add what is needed. Less firefighting. More focus. What you will notice: fewer tickets, faster fixes, and tech that is quietly brilliant in the background. Talk to us:
If anything in this edition sparked a question or you would like help setting up a feature, book a quick session with us at avensystech.com.
