Even the giants can stumble. Microsoft recently made a change that broke core functionality in Outlook calendar invites. For years, you could add a professional signature, even with an image like a logo or headshot, and the invite would save without issue. After their “update,” any invite with an image fails to save. The only way around it is to strip your brand from your signature, or manually delete the image every single time. That is not a solution. That is sloppy UAT and a failure to protect customers from unnecessary friction.

When I raised it, Microsoft support offered me three “options”:

1. Remove signatures as a default from email so they do not flow into invites.
2. Remove images from the signature altogether.
3. Continue deleting the images manually every time I schedule a meeting.

None of these preserve the professional experience customers expect. And none of these should be acceptable when the problem was created by Microsoft in the first place!

What struck me most was what the agent said to me directly: “My options as your ambassador are limited, and as much as I would want to, I don’t have the capability to have this fixed.” That sentence says everything about the culture. The agent cared, but was boxed in by scripts, stripped of escalation paths, and left to repeat “workarounds” that do not actually work. That is not support, it is resignation.

Here is the lesson for every company:

• Test before you break. Core functions should never be compromised by poorly run changes.
• Prioritize what matters. If it disrupts customer workflows, it is not “low priority.”
• Empower your agents. Scripts do not solve problems, people do. If your frontline cannot escalate, you have trapped them and your customers in frustration.

I am not riding on a corporate license, I am a paying business customer. That means they should care about my experience and my satisfaction. Instead, the silence is deafening. And the sad truth is, when a company is making big money, too often the big misses do not seem to matter. Whether you are Microsoft or a small business, care is never optional.

I’d love to hear your thoughts, have similar situations? What thoughts do you have on how companies do better and prioritize the customer experience? Do write to me and let's brainstorm together on ways we can improve them!