← Documentation

Troubleshooting

Common issues and fixes for end users, plus architecture notes on Outlook performance and memory behavior for IT and security reviewers.

Common issues and fixes

Clevermore isn't in the Outlook ribbon

The add-in appears in the Home ribbon once it's installed. If you don't see it:

  • Restart Outlook. Newly-deployed add-ins are picked up at the next launch.
  • Open Get Add-ins → My add-ins and confirm Clevermore is listed and enabled.
  • If your firm deploys add-ins centrally, ask your IT administrator to confirm the assignment for your account in the Microsoft 365 Admin Center.

Sign-in fails or loops back to the start screen

Clevermore signs in using Azure AD with the Microsoft Graph permissions your administrator approved. If sign-in fails:

  • Confirm your account is signed in to Outlook itself with your work credentials.
  • Tenant-wide admin consent must be granted for the Clevermore enterprise application before any user can sign in. If you're the first user in your firm to try Clevermore, this step is likely outstanding.
  • Reload the taskpane (right-click inside it → Reload) to clear any stale auth state.

New emails aren't producing tasks

Clevermore is selective by design — not every email produces a task. If you expect a task and don't see one:

  • Give it a minute. Analysis runs server-side after the email is received and a new task can take a moment to appear.
  • Open the email and use the Clevermore taskpane's Re-analyze action to force a fresh pass.
  • If the email is purely informational (no ask, no commitment, no deadline), Clevermore intentionally won't create a task for it.

Categories or matter folders aren't appearing

Clevermore writes categories and matter folders directly into your mailbox via Microsoft Graph. The first sync happens shortly after sign-in.

  • Refresh your folder list (F9 on Windows) to pull the latest changes from Exchange.
  • Check Categorize → All Categories… for entries starting with 💼 (matters), 🔴/🟠/🟡/⚪ (priorities), or 📋/📨 (classification/source). If they're missing, sign out and back in to trigger a re-sync.

The taskpane feels slow or unresponsive

  • Reload the taskpane (right-click inside it → Reload) to drop any stale state.
  • The taskpane is a web view — a slow corporate proxy or unstable VPN can stall network requests. If other Microsoft 365 web surfaces are also slow, the network is the most likely cause.
  • Restart Outlook. This recycles the WebView2 host that the add-in runs in.
  • If the problem persists, email support@clevermore.ai with the approximate time and your account email so we can look at server-side traces.

Outlook performance impact

Clevermore is a Microsoft 365 web add-in. It does not run inside the outlook.exe process. The taskpane is rendered by WebView2 (on Windows) or WKWebView (on macOS) as a separate process managed by the Office add-in host.

  • Outlook launch time. Web add-ins are not loaded at Outlook startup. The taskpane process is created lazily — on first taskpane open, or on the first message-send event if the add-in has an OnMessageSend handler. Cold Outlook launch is unaffected by Clevermore.
  • Memory footprint. The taskpane runs in a WebView2 process whose working set is bounded by what the page allocates — typically tens of MB for our bundle. This memory is reclaimed by the OS when the WebView2 process exits (taskpane closed for an extended period, or Outlook shutdown). Outlook's own working set is unaffected because no Clevermore code is loaded into outlook.exe.
  • CPU at idle. The taskpane is event-driven. When idle, JavaScript timers are throttled by WebView2 and CPU use is effectively zero. There is no background polling of the mailbox from the client — analysis happens server-side after Exchange delivers messages.
  • OnMessageSend latency. When the user clicks Send, Outlook awaits an asynchronous handler that performs a small server round-trip. We bound this on the server side to keep send-time latency imperceptible. If the network is unreachable, the send proceeds rather than blocking.

Reviewers can verify any of the above directly with Windows Performance Monitor, Task Manager, or the WebView2 DevTools — Clevermore's process is visible as a child WebView2 process under Outlook.

Memory leaks — why web add-ins avoid VSTO's historical problems

VSTO (Visual Studio Tools for Office) add-ins were the dominant model for Outlook extensions for years. They are also the source of the memory and stability problems many firms still associate with Outlook add-ins. The web add-in architecture Clevermore uses is structurally different.

How VSTO leaks happened

  • VSTO add-ins are loaded directly into the outlook.exe process as in-process COM components. The add-in and Outlook share one address space, one garbage collector, and one process lifetime.
  • Outlook objects (MailItem, Explorer, Inspector, etc.) are COM objects with reference counts. Add-ins that forget to release them with Marshal.ReleaseComObject pin those objects in memory for the rest of the Outlook session.
  • Event handlers wired to Outlook events hold strong references back into the add-in's managed heap. Forgetting to unwire them keeps the entire object graph alive.
  • Because everything is in one process, leaks accumulate over the lifetime of outlook.exe. The only remedy is to restart Outlook.

How web add-ins are different

  • Clevermore never loads code into outlook.exe. The add-in runs in a separate WebView2 process spawned and managed by the Office host.
  • There is no COM marshaling between the add-in and Outlook's object model. All access goes through the sandboxed Office.js bridge with structured-clone serialization — there are no shared references to leak.
  • The add-in's memory is bounded by the WebView2 process. When Outlook closes, the OS reaps the process and reclaims every byte. A misbehaving add-in cannot grow Outlook's working set.
  • If the taskpane process ever crashed or hung, only the taskpane would be affected. Outlook itself keeps running.

Microsoft's guidance on this architecture is documented at Office Add-ins overview and Privacy, permissions, and security for Office Add-ins.

For IT administrators

For tenant-wide consent, centralized deployment, or removal, use the Microsoft 365 Admin Center and the Microsoft Entra admin center. To remove every trace of Clevermore from a user's mailbox, see the un-enrollment guide.

For anything not covered here — including deeper architecture or security reviews — contact support@clevermore.ai.