Outlook and Windows 10 — Common Questions and Answers

Many businesses have begun upgrading to Windows 10 since it was made available free of charge for Windows 7, 8, and 8.1 users. Different companies have chosen to convert for different reasons–some see it as part of a push for more modern computer infrastructure with better official support, while others prefer the synchronization of having the same operating system on their computer as is on their Windows Phones. Many apps, like Office 2016, function more or less identically on both phones and PC, which makes it easy for individuals with mobile devices to share apps and data between the two.

Whether your personal shift to Windows 10 also brings with it a shift to Office 2016 or not, you may find yourself a little lost due to system-wide changes and adjustments. Some functions your business relies on may have turned themselves off, changed, or just stopped working altogether. One example is Microsoft’s Business Contact Manager, an Outlook-based CRM system, which is no longer supported by Office 2016. If you use Microsoft Outlook or Office 365, this article addresses some simple fixes to some of the most commonly faced issues when upgrading to Windows 10.


The Basics

Since Windows 10 is a new operating system, sometimes even the most basic functions change location and become harder to find after installing. If you can’t find your Outlook or Office installation, can’t print, or can’t manipulate files, use these simple fixes.

Can’t Find Outlook or Office

Make sure your Windows 10 installation is current, as this was fixed in a recent patch. Run Windows Update or Microsoft Update and this problem should solve itself.

Can’t Load or Save Files

An update is coming that should fix this issue, which seems to have something to do with OneDrive. Microsoft also has a few workarounds available on its help forums.

Office or Outlook Crashes Immediately

This most commonly happens to users of Avast! Antivirus. If this applies to you, update Avast to a more recent version and the crashes should stop.

Can’t Print After Upgrading

Some printer drivers are not compatible with Windows 10, even if they were compatible with 7, 8, or 8.1. Update or reinstall your printer drivers and you the printers should become functional.

Outlook Won’t Send or Receive Mail

As with being unable to find the program, this was fixed in a recent patch. Make sure your Windows 10 installation is current, and run Windows Update or Microsoft Update if not. If this doesn’t work, go to the Start menu and find “Command Prompt (Admin)” or “Windows PowerShell (Admin).” In the resulting window, type “Sfc /scannow” and wait. This process takes about 20 minutes, after which you should reboot your computer and restart Outlook.

Lost in Upgrades: How to Retrieve Old Functions or Handle Common Errors

The first few times you run Windows 10, your Outlook or Office 365 programs might throw up unfamiliar errors or behave erratically. Most of the issues can be fixed easily.

Software Activation Not Valid

Sometimes, upon being loaded in Windows 10 for the first time, a licensed program like Outlook or Office 365 will believe its license is no longer valid. Close any attempts at opening the program, go to the Control Panel, and click on Programs and Features. Select the program you tried to run and click Change, then Quick Repair. This will force it to validate itself, and should fix the issue.

No Email Notifications

Stopped receiving email notifications? This fix is very simple. Go to the Action Center and click on All Settings, then click on System. The panel to the left should have a Notifications and Actions section. Click here. You should see a section labeled Show Notifications From These Applications. Click on Outlook, and make sure all of its notifications are turned on.

Missing Search

Unlike most of the other problems on this list, a lack of results when using the search function in Microsoft Outlook requires no intervention from the user at all. Simply let the computer idle for a while and it will create a new index of search terms. If this doesn’t work, consider going to the Control Panel, and under Indexing Options, use the Rebuild or Reset options under the Advanced tab. This will force the program to rebuild its search index.

Can’t See Pictures

Are important pictures or other attachments not showing up in your emails? It’s likely that a problem with a registry value is the cause. As incorrect or inappropriate registry edits can seriously compromise a computer’s stability, you should use Microsoft’s step by step guide to solving this issue.

Other Fixes Aren’t Working

Facing one or more issues and not getting results from these? Unsure of how to proceed, or not finding your answer here? Download the Microsoft Office Configuration Analyzer tool (OffCAT) and run it. This program, available from Microsoft’s official website, goes through your installed Microsoft Office programs and finds known configuration problems or errors. While it won’t fix the issue directly, it will provide a link to an article that goes through the problem in greater detail and provides possible solutions. If you are at your wits’ end with an Office problem, whether or not it involves Outlook, OffCAT can help.

What About Third-Party Add-Ins?

Most add-ins you use, regardless of your previous operating system, will continue to function in Windows 10. The architecture used in Outlook in Windows 10 is similar to that which has been used since at least Windows Vista, so add-in compatibility should not present an issue. If any of your add-ins are essential to business functions, however, contact the vendor or creator to make sure these add-ins will still work after you make the switch to Windows 10. iCloud, however, has some unique problems, so here is a fix and some general advice for erratic add-in behavior.

iCloud Failure

Sometimes the official iCloud add-in stops working after users make the switch to Windows 10. If this happens to you, navigate to File, then to Account Settings, then to Account Settings…,, then to Data Files, and remove iCloud. Make sure that you are totally disconnected from iCloud, then exit Outlook and turn off all iCloud features in the iCloud Control Panel. Make sure you have the latest iCloud installation, and if you do, repair iCloud in the same manner as described above for the Software Activation Not Valid error. Then go to the iCloud Control Panel again, turn on all the features again, and restart Outlook.

Erratic Add-in Behavior

If your add-ins are behaving erratically or are just downright not working, try disabling them and restarting all Office programs after doing so. If this reduces or eliminates the problem, try uninstalling these add-ins and reinstalling them. It’s possible they relied on a resource which moved during the installation of Windows 10, or were damaged during the upgrade. Either way, this will get the program up and running again–or at least speed up the process.

It’s Been a While

The new features of Windows 10 have made it a popular upgrade choice, and some users are upgrading all the way from decade-old OS configurations like XP and Windows Vista. For these users, Windows 10 marks a fundamental change in the way Windows works, and while many things are similar, many have changed as well. Some features have also been added, and some work differently. If your business is considering making the switch to Windows 10, go in prepared for these new features and changes.

New Right Click Menus

The menu shown when right-clicking on Outlook (or any program) in the taskbar has changed in newer builds of Windows, providing additional operations such as taskbar pinning. If you need a command from the old right-click menu, hold Shift while clicking. This will bring up the classic view seen since Windows 95.

This change also applies to shortcuts. If you’re used to right-clicking a shortcut to run Outlook as an administrator, simply hold Shift during the click.

Cascade and Tile Changes

Many users of Outlook in older editions of Windows used the cascade and tile functions to arrange windows appropriately. These features are still present in Desktop mode in Windows 10, but are somewhat harder to find. To use these features, minimize all windows, then click on each Office or Outlook window you want to cascade or tile. Then right click anywhere on the taskbar other than the Start button, and click on “cascade windows,” -> “show windows side by side,” or “show windows stacked.” This will arrange all currently active windows to your choosing.

Integrating Windows Updates and Office Updates

One new option available in Windows 10 is to use the same update infrastructure to perform security and functionality updates for Office as well as for Windows core features. This can help keep your data safe and your programs running effectively. To switch this update method, visit the official page for Microsoft Update.

Any Other Issues?

These are some of the most common issues faced by Outlook or Office users when upgrading to Windows 10, and we’ve attempted here to discuss changes in features or alternative methods for doing routine tasks provided by the new operating system. If you encounter an issue that isn’t covered here, check Microsoft’s official Office support site for new fixes and deeper answers. If your issues have more to do with Windows 10 functionality than Microsoft Office specifically, Microsoft offers a focused support site for those issues as well.

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