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Employee Keeps Flagging IT’s “Anti-Phishing” Emails As Phishing, Chaos Ensues

by Annie Nguyen
November 2, 2025
in Social Issues

Companies invest in phishing awareness to shield data, training staff to spot urgency, odd links, or sender mismatches. Tests reinforce vigilance without real risk.

One worker failed a drill using job-required social media, enduring extra sessions. Soon, the IT director flagged a quiz deadline via attachment. Hover previews raised flags, prompting reports.

Clarifications arrived, yet patterns persisted. Does the caution loop endlessly? Scroll down for the high-importance chain and Redditors’ rule ideas.

One cautious employee turned mandatory phishing training into an endless report loop on the IT director’s own emails

Employee Keeps Flagging IT’s “Anti-Phishing” Emails As Phishing, Chaos Ensues
Not the actual photo

My IT Directors emails look awfully suspicious?

Three months ago, my company held a two-hour seminar

about email phishing and how to prevent it.

This seminar also came with an update to our email software.

The software now has a preview feature; if you hover over a link, it opens a preview of the page.

Anyway, I got an email from our “IT Director”

saying I was in violation of their internet policy for using social media.

Using social media is literally part of my job.

But I was stupid and opened it. It turned out to be a phishing test.

They made me sit through another two-hour seminar.

That same week, I got another email from our director.

It was "sent with high importance".

Subject: Phishing Email Test. “Hello everyone, this is a reminder to stay aware of phishing emails.

Please review the PDF guide and take a short quiz (link) to test your skills by 5pm.

Thank you, (IT Director’s Name)”

Now, on that email’s attachment, one of the "signs of phishing" was

"If the email pressures you to click a link."

So I thought, “This fits perfectly.” I decided to report it as phishing.

An hour later, I got another email from the director.

Subject: Reporting Emails. “Hello everyone, We have received numerous phishing reports about the email about the phishing quiz.

Please note, any email sent from (IT director’s email) is not phishing.

We have included a new link for your convenience. Thank you, (IT Director’s Name)”

To me, this new email looked even "more" suspicious than the last one.

So, naturally, I reported it again. I’ve been doing this for over two months now.

Every time, everyone gets another email saying, “This email is not phishing.”

Please, for the love of everything, don’t make us sit through another two-hour seminar.

Phishing awareness campaigns often use simulated attacks to test employee vigilance, but they can accidentally mimic “real” threats. That confusion leads to repeated reporting and frustration.

According to the 2023 Verizon Data Breach Investigations Report, analysts reviewed 16,312 incidents, including 5,199 confirmed data breaches, and found that social engineering remained one of the most common tactics used by attackers.

The IT director’s emails, marked ” high importance” and urging immediate action, show common pitfalls. Time pressure and urgency are classic red flags taught in phishing training.

This irony weakens trust. Employees like the original poster apply what they learned correctly. Yet they’re told they’re wrong through clarifications that sound like real phishing messages.

For example: “Please note, any email from [address] is not phishing.” That kind of statement mirrors actual scam tactics.

The repeated cycle of reporting and rebuttal over two months shows poor program calibration. Proofpoint’s 2024 State of the Phish report noted that unclear simulations often cause confusion and false reports, wasting resources and breeding cynicism.

In this case, the director’s failure to pre-announce tests and lack of distinct branding, like “Simulation” in the subject line, broke best practices from NIST. NIST’s Cybersecurity Framework recommends transparent debriefs that reinforce learning, not defensive confusion.

The original poster’s persistence was ideal. They followed protocol perfectly by reporting suspicious messages. SANS Institute guidelines say employees “should” report any suspicious email, even internal ones.

According to IBM’s 2022 report, spoofing internal domains is a common feature of advanced phishing campaigns. Research from KnowBe4 also suggests that positive reinforcement, such as rewarding accurate reports, is more effective than punishment in reducing phishing clicks.

To fix this, IT leaders should review the simulation balance between realism and confusion. They should use clear sender signatures like “[email protected]” and share analytics openly afterward.

If employees feel fatigued, anonymous feedback channels can help. That aligns with OSHA’s stress mitigation policies under the General Duty Clause.

Ultimately, a strong cybersecurity culture grows through respect and iteration. Employees who report are assets, not annoyances. Celebrating them builds vigilance without burnout.

Here’s the feedback from the Reddit community:

Redditors laughed about accidentally flagging real cybersecurity drills as scams

Gaosnl − I’ve had the same. During a survey in preparation for a team-building meeting,

they asked about our favorite food and movies. Half of us reported it as social engineering.

Infinity293 − Heh, my work signed us up for some phishing training but forgot to warn us.

The email was sent from an external sender at 2:45 a.m. telling us to click the link,

so naturally, we reported it as phishing.

Ziogref − Our work used to send company-wide announcements via email with links.

Then IT security started doing phishing tests in the exact same format,

and a bunch of us reported them to themselves.

I certainly did. Took a couple of months before they changed the format.

Users roasted the “my email is safe” line as classic phisher behavior

mizinamo − “Please note, any email sent from: (insert IT director email here) is not phishing.”

That’s exactly what a phisher would say.

DoctorGuvnor − Of course you’re going to get a “this is genuine” email, what would any phisher do?

You could probably keep this going until the director comes to each desk individually and tells you.

Commenters joked about auto-flagging every IT director email out of caution

Telvyr − Reply saying you’ve compiled a list of suspicious emails,

link it to their own cyber training page, and send it back.

That’s the perfect level of malicious compliance.

HMS_Slartibartfast − Since you’ve received multiple suspicious emails from the same address,

set up a rule to automatically mark all emails from that sender as phishing.

Then warn your coworkers to do the same, can’t be too careful these days!

Redditors mocked phishing tests that outsmart their own creators

Joshslayerr − My university sent out phishing test emails every year.

Almost everyone failed, then they sent a “you passed, skip the seminar” email,

which turned out to be another test.

That caught the rest of the people. I passed only because I never check my work email.

benkenobi5 − I literally got a phishing test from the real IT department.

I clicked the link, and it rewarded me with more training.

Now I just ignore everything unless it’s from my supervisor, works great so far.

JoeyJoeJoeJrShab − The people making phishing training emails

love sending stuff that looks exactly like phishing.

One coworker even opened the link in cURL to be safe, and still had to take the remedial training.

One deadline became a delightful do-loop, proving training works, maybe too well. Would you keep reporting or request clearer headers? Drop your inbox insurrection tales below!

Annie Nguyen

Annie Nguyen

Hi, I'm Annie Nguyen. I'm a freelance writer and editor for Daily Highlight with experience across lifestyle, wellness, and personal growth publications. Living in San Francisco gives me endless inspiration, from cozy coffee shop corners to weekend hikes along the coast. Thanks for reading!

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