When Trust Breaks: Why You Need to Go Over the Heads of Customer Support

We're seeing a wave of high-profile customer‑service failures this month that reveal one thing: support teams are overloaded, AI is often unaccountable, and customers are left helpless.

🔥 Recent breakdowns in trust and service

In mid‑July Microsoft suffered a 19‑hour global outage of Outlook and M365 Copilot, locking out millions from email, Teams, calendars—and leaving business productivity tanked. Companies scrambled to rely on backup plans—or learned they had none.

In the UK, EE, BT and Vodafone users couldn't make or receive voice calls for three days in late July; call centers were also down and communication was minimal.

At Hertz, a customer had a video showing no damage—yet an AI system flagged a water reflection as damage and the rental location refused to let him dispute it. He called it "unchallengeable" automation.

Peppermayo, a fast‑fashion brand, is being slammed for unfulfilled orders and poor customer service, while influencers were whisked off on lavish trips. Complaints are skyrocketing and refunds are delayed.

When systems fail, companies rarely make it easy to reach real decision‑makers. Smart execs know this leads to wasted time and eroded trust.

🚨 What do these breakdowns teach us?

• Automated systems fail in unaccountable ways. AI can speed up work—but when something goes wrong, good luck contesting it.

• Contact centers are brittle. Replicas and scripts are overloaded or offline when failure happens.

• Delayed transparency fuels frustration. Whether it's hats on answering phones or hiding call moves overseas, delays in communication break trust.

Verint's 2025 CX survey says half of consumers believe brands are missing expectations—and 74% would switch after one bad experience.

✍️ How to Escalate When Support Won't Help

When you've been ignored or stuck in looped auto‑responses, you need to go above the support layer:

• Write directly to executives. That's where real power—and accountability—lives.

• Use the DearCEO.wtf email builder to craft a clear and respectful message that gets noticed—no support ticket needed.

• Attach clear evidence: order numbers, timestamps, screenshots, or video that supports your case.

• Be polite‑but‑specific: explain the issue, the impact on you, and what outcome you expect (refund, repair, apology).

• Send the email to executive addresses (whenever available) and bump it after 3–5 business days if ignored.

✅ Real‑world wins

Customers who've faced these big failures—Microsoft, Hertz, Vodafone, Peppermayo—often report no easy pathway to resolution via customer service. But an executive appeal can change that. When support agents are blocked by policy, execs can shift it. And they see reputational risk first.

Final thoughts

Technical failures will happen—clouds go down, AI misreads a reflection, networks glitch. When that happens, the support chain can break. That's why having a direct escalation path matters. When everything else fails, a well‑crafted, executive‑facing email often breaks the logjam. Use tools like the DearCEO.wtf builder to make your voice count, even when support won't help.

Remember—good customer service shouldn't require escalations. But if you've been stuck, ignored or ghosted, going over heads is your best option. And with a little help from the DearCEO.wtf builder, it's easier than you'd think.