"Format picture" has disappeared from Outlook Mac
I use the Outlook app on 3 different MacBooks. Two have recently auto-updated Outlook to version 16.102.2, and I've lost the ability to format a picture in the body of an email. I use lots of screenshots in emails, and always put a border around them to clearly differentiate them from the body text. Right-click the image and select Format Picture from the menu. I can still do it in the third MacBook which is running Outlook version 16.84.2. I don't know if the latest update is meant to be an improvement, but I'm not happy about it! I'll turn off automate updates for the third MacBook. Not sure if I can revert the other two to version 16.84.2 - does anybody know if this is possible. Also wonder if users of the Windows app have experienced the same loss of the Format Picture feature?
Synchronization issue in New Outlook for Mac – ״Failed to refresh subscriptions.״
Hello, I am using Microsoft 365 (Exchange Online) on Mac, running macOS 26.1 (Tahoe). My Outlook client is: Outlook for Mac Version 16.103.3 (25113013), with a Microsoft 365 Subscription license. Since yesterday morning, in the New Outlook interface, my inbox has suddenly appeared empty, and I constantly receive the following error message: “Failed to refresh subscriptions.” It’s important to note: In Legacy Outlook, everything works perfectly. The web version and the Outlook app on my mobile phone also work well. The issue persists regardless of the network I am on (home, office, cellular, etc.). Troubleshooting steps I already tried: • Updating Outlook to the latest version • Removing and re‑adding the account • Clearing cache and preferences • Formatting my Mac and reinstalling everything from scratch Unfortunately, none of these steps has resolved the issue. Is this a known bug, and is there a recommended workaround or an upcoming fix? Appreciate assistance on that issue.Outlook for Mac not showing attachments in a separate window
When composing an email in Outlook, all added attachments are visible in the main interface. However, once I pop out the message into a separate window, the attachment section becomes blank, and I can no longer see the files I’ve attached. Environment: Microsoft Office for Mac Version 16.103 (25110922) OS: Tahoe 26.0.1 MacBook Pro 14 M4 Pro (Nov 2024) In Main Interface: In a Separate Window
Open links in the Edge profile associated with the Outlook account
There is a setting in Microsoft Edge on macOS under Settings > Profile > Profile preferences labeled "Open external links in another profile when recommended by external applications". It seems like it ought to be possible for Outlook to "recommend" that a link in an email in my work account be opened in the Outlook profile signed in with my work account, and likewise for my personal account. How would one go about enabling that? I'm using Outlook for Mac version 16.103, and Edge version 140.0.3485.94, on macOS Sequoia 15.7.1. Thanks!Outlook for Mac (Paid Version) – Dozens of Challenges, Any Suggestions?
I don’t think I need to repeat what most of us already know: Microsoft’s in-app Outlook support is incompetent at best, misleading at worst. And so are all other Microsoft channels one can tap in to for support. The so-called “experts” loop the same scripted answers, suggest fixes that cause new problems, or simply stop replying. Tickets are closed prematurely (likely KPI-driven) without solutions, or left hanging with “we’re still working on it” updates every few weeks. My oldest ticket like this is now in month 4. Outlook for Mac feels like a paid beta test, and we are the paying beta testers. My Mistake (Following Bad Advice) On the advice of an in-app “expert,” I moved from Classic Outlook to the New Outlook after my IMAP accounts started duplicating files (Title-of-File 28 and so on). When the New Outlook began breaking down too, I tried switching back. That’s when I lost: My entire address book All reminders Other important data Now I’m stuck in New Outlook, with Classic no longer an option without risking more loss. Where I Am Now I’ve raised a dozen+ tickets and used the in-app support multiple times (currently broken in my Outllook since months). Each time, I asked for a real Mac Outlook expert or higher-level support. Instead, I’ve ended up with a list of about two dozen bugs and broken features (which I’ll share separately). I even sent this list with a letter requesting a real expert and a level-two support person. The result? A kind but non-expert agent. I ticked the box for email contact (which always results in a phone call), then they want screen sharing, then they offer useless answers, show they did not read thoroughly… and the loop begins again. My Main Question Right now, my top priority is: How can I safely revert back to Classic Outlook without losing data? I need a reliable way to back up everything in New Outlook first, so I can restore if things go wrong. The backup option in New Outlook is greyed out. When I asked support, their advice was literally: “Switch back to Classic and make the backup there.” I know… After months of tickets, I still don’t have a safe, confirmed backup/restore method. Why I’m Posting Here I no longer trust Microsoft’s “experts.” And I won’t experiment blindly with their suggestions until I know I can restore my data safely. So I’m asking this community: Has anyone successfully reverted from New Outlook to Classic without losing data? And how did you do this? How did you back up first? Are there tested workarounds for these problems, or is the only realistic option to abandon Outlook for Mac entirely? Any tested, real-world advice would be much appreciated. Thanks. PS and yes, I am on the latest Mac OS and Outlook version. Here is the doc submitted to MS: Subject: Escalation Request – Outlook for Mac Issues Dear Microsoft Support, First, I kindly request that this case be assigned to an agent with full Outlook for Mac expertise. So far, most of the agents I have spoken/dealt with seem more Windows-focused or not fully trained in Outlook for Mac. Important Notes Before Troubleshooting Pleasedo not suggest reinstalling Outlook or switching back to Legacy without addressing the risks outlined below. I havenine IMAP accounts (no POP accounts). When I previously followed support advice to create a new identity and reinstall Outlook, I lost all reminders and address book entries. I only managed to recover them by restoring from Time-Machine. This was unacceptable and must not happen again. If reverting to Legacy is necessary, I need aclear guarantee that no emails, reminders, or contacts will be lost. The reason I initially left Legacy was because of persistent folder duplication (e.g., folders named xx17 and higher) and your agent said this would be a good solution. Unless there is a permanent fix for this, reverting is not a viable option. Enclosure: Detailed Issue List – Outlook for Mac (Office 365, Commercial) A. Data Loss Risks & Backup # Issue Description Requested Fix Severity 1 Returning to Legacy Reverting risks data loss (reminders, contacts, calendar). Legacy also created random duplicate folders (xx17, xx18, etc.). Guarantee safe revert without data loss or folder duplication. High 2 Backups Export/backup option is permanently greyed out. Legacy allowed full backup. Enable backup/export for accounts, reminders, contacts, etc. High B. Search & Synchronization # Issue Description Requested Fix Severity 3 Search Failures (Visible Emails) Search fails to locate emails that are clearly present. Fix search reliability. High 4 Search Failures (Disappearing Emails) Emails vanish from search though retrievable via a deep search in UBF8T346G9.Office folder. Ensure Outlook search indexes all mail consistently. High 5 Reply/Sending Failures - Some messages stuck as “downloading” - Some messages hang in Outbox and can’t be deleted. Fix sending/reply bugs and allow removal of stuck messages. High 6 Duplicate IMAP Folders Some IMAP accounts show extra Inbox or Archive folders. Clarify origin and safe removal. Medium C. Email Functionality & UI # Issue Description Requested Fix Severity 7 Viewing Replies Legacy showed sent replies via a button; grouping in new Outlook is inconsistent. Restore a reliable way to view replies. Medium 8 Incorrect Sent Mail Count Unified Sent box shows “4,294,967,295” messages. Correct message count. Low 9 Replies Disappearing Some email replies disappear entirely unless found via deep file search (see 4). Prevent loss of replies. High 10 Attachment Indicator Emails with attachments no longer visually marked. Reintroduce indicator. Low 11 Outbox Editing Emails in Outbox cannot be opened/edited offline. Restore editing functionality. Medium 12 Categories Greyed Out Categories unavailable for IMAP inbox emails. Enable categories for IMAP. Medium 13 Trash Behavior Some emails vanish immediately after moving to Trash. Keep items until manually deleted. Medium 14 Restoring Deleted Emails Cannot drag emails from Trash back to Inbox. Allow restoring deleted items via drag/drop. Medium D. Calendar, Contacts & Reminders # Issue Description Requested Fix Severity 15 Teams Meeting Reminders Meeting reminders lack join links; accepted invites sometimes show as unconfirmed. Restore full functionality of Teams invites/reminders. Medium 16 AppleScript Support Commands like IMAP and Account appear in dictionary but don’t work. Restore full AppleScript functionality. Medium 17 Contact Autofill Stored names don’t appear in search/autofill. Fix contact lookup. Medium 18 Duplicate Contacts Contacts duplicate sometimes automatically; removal must be manual. Provide bulk de-duplication or stop auto-duplication. Medium 19 Duplicate Reminders Reminders duplicate sometimes automatically, removal must be manual. Provide bulk de-duplication or stop auto-duplication. Medium 20 Contacts Toolbar Cannot customize toolbar in Contacts. Enable customization. Low 21 Adding Contacts Cannot add email address to contacts by clicking it (was possible in Legacy). Restore this feature. Medium 22 Calendar Conversion Legacy allowed emails to be converted to calendar entries. Restore feature. Low 23 Calendar Invites Invites not available unless sent to primary account. Support invites across all accounts. Medium E. Notifications, Updates & Misc. # Issue Description Requested Fix Severity 24 In-app Support Not Working In-app Outlook support is non-functional and has not provided useful responses. Confirm why it fails and provide a working alternative. Medium 25 Support Notifications Daily pop-up about “Customer Support activity,” even when none exists. Feature now broken. Stop or fix notification. Low 26 Frequent Update Pop-ups Update window appears too often. Allow disabling or limiting update prompts. Low F. Support Experience & Compensation # Issue Description Requested Fix Severity 27 Support Experience Agents missed appointments, gave copy-paste answers, and closed unresolved cases. Improve continuity, assign competent Mac agent, ensure accountability. High 28 Compensation Request More than 20 hours lost on missed calls, repeated troubleshooting, and unproductive sessions. Confirm process for requesting compensation for lost time and effort. See below. High Request for Resolution and Compensation Given the number and persistence of these issues, Outlook for Mac (Commercial) feels under-tested and unstable despite being a paid product. I have already spent more than 20 hours waiting for promised calls, writing follow-up emails, dealing with answers that regress, non-Mac trained agents, bad copy-paste answers, attempts by agents to close unresolved issue, and troubleshooting without resolution to name a few. I feel like an unpaid and poorly treated beta tester! I request: Escalation to an Outlook for Mac expert. Clear guidance on safe backup/recovery for contacts, reminders, and accounts. A statement on how I can requestcompensation for this buggy application, the time spend and the ongoing headaches it gives, to name a few. Maybe the easiest is to cancel the need to pay the licencing fees. Please confirm the appropriate channel for submitting this claim unless you are authorised to so immediately, which I hope for simplicity’s sake you are. Thank you for your attention. I look forward to your prompt and constructive response.
Constantly being asked to reauthenticate accounts in Outlook for Mac
Hey everyone, I started running into a strange issue a few days ago. I am using Outlook for Mac Version 16.102.1 (25101829) with seven accounts configured. Out of nowhere, I keep getting repeated prompts to reauthenticate all my accounts. I use the Microsoft Authenticator app on my iPhone, get the push notification, approve the two digit code, and everything goes through fine. A few hours later, Outlook shows the same pop up again asking me to reauthenticate. I have gone through this process at least ten times now, and it keeps happening. Is anyone else seeing this issue or found a fix?
Outlook for Mac inserts signatures at the very end of an email chain
Hi community, This seems to be a new issue caused by an Outlook for Mac update in recent months. When reply to an email, the default signature is inserted to the very end of an email chain instead of the end of the reply one is about to draft (in other words, above the attribution "On <data>, <name> wrote ..."). I can currently work around this issue by enabling "when replying or forwarding, use the format of the original message" (under Settings -> Email -> Composing). This seems to be a bug.
Run rule now is grayed out
My rules in Outlook are grayed out again. The part of manual execution. And this status has been remained for at least 3 days. I encountered this circumstance before like few months ago and here we go again. My account is personal account (Outlook.com). When I use Microsoft Outlook for Mac, Version 16.101 (25091314), to see my rules and wanna execute one of the rules, it's greyed out, a.k.a, cannot be executed. When I open a browser, say Edge, (Version 140.0.3485.66 (Official build) (arm64)), the same status as well. My findings so far: All of rules that will categorize email cannot be executed manually now. Rules that will delete emails can be executed manually. It's manual execution that won't work. Coming emails will still be categorized by the rules automatically. Any clue how to solve this? Or somewhere is wrong internally in the system so far?
Outlook for Mac quote button
Hi all, It has been a few months since I migrated to MacOS from Linux. During my days in Linux, I use Outlook web version and now I have been using Outlook app for Mac. One feature that I missed is quote button, which I use quite a lot! It seems that the Outlook app in Mac doesn't have quote button, for some reason. What I usually do is copy pasting and then put an indentation and italic, which is OK, but not nearly as polished. It would be really great to have this feature added in. In the meantime, is there any alternative to 'save' a style for quote that is similar to the web version? Thanks!
