Office “Any Attachment” Andy – The Colleague Who Never Sends the Right File
Office “Any Attachment” Andy is the co-worker who confidently emails the wrong file every time. Despite countless training sessions, he’s sent incorrect stats, blank documents, and even animal photos to the CEO
Office Mugshots – Series 1
Office “Any Attachment” Andy: Officially Booked & Charged
Welcome back to the Office Mugshot Collection – Series 1, where basic workplace skills are repeatedly explained, carefully documented, and then completely ignored.
Today’s offender is a man who has typed the phrase “Please see attached” more times than anyone in recorded corporate history — despite rarely attaching the correct thing.
Ladies and gentlemen, meet Office “Any Attachment” Andy.
James Mason
📸 The Mugshot
Captured moments after Andy realised — once again — that the file he meant to attach is not, in fact, the file he attached.
Seen clutching his charge board in visible distress, Andy appears mid-meltdown: a man confronting the crushing reality that training number seven also didn’t stick.
🗂️ The Crime
Chronic Attachment Failure
Andy’s entire professional reputation is built on confidently sending emails that contain either:
- The wrong document
- An outdated document
- A completely unrelated document
- Or absolutely nothing at all
His emails arrive polished, friendly, and professional — until the recipient opens the attachment and realises they’ve been sent last year’s stats, a blank spreadsheet, or something personal that was never meant to leave Andy’s desktop.
James Mason
📁 Case File Highlights (HR Notes)
CASE FILE NO: 2025-AA-001
Time of offence: 16:52
Location: Desk nearest the printer (and rising panic)
Victims:
- Clients await accurate data
- Senior leadership
- Colleagues dragged into damage control
- Andy himself
Method:
Confidently clicking Send before checking the attachment — or attaching something and trusting fate to sort it out.
Motive:
“Thought I’d attached it” (unverified)
Frequency:
- Logged incidents: 47
- Unreported near-misses: Countless
- Mandatory training sessions attended: Enough to know better
Witness statements:
Colleagues report Andy freezing at his desk seconds after sending, staring at his screen and whispering “No… no… no…” before reopening Outlook with visible regret.
Security footage notes:
Andy is seen:
- Opening the Sent folder immediately
- Slumping back in his chair
- Sending a follow-up email starting with “Apologies — please see correct attachment below”
- Attaching the wrong file again
Escalation record:
One confirmed incident involving:
- Incorrect statistics were sent to a client
- A correction email
- A second correction correcting the correction
- And, inexplicably, animal pictures accidentally emailed to the CEO
James Mason
await
🔢 Number of Times the Wrong File Was Attached
Official count: 47
Unofficial count: Nobody knows anymore
Andy’s estimate: “Not that many, surely?”
Despite numerous reminders, step-by-step guides, screen-share walk-throughs, and a laminated checklist, Andy continues to attach files as if it were a random experiment.
James Mason
📉 Cost to the Business
Andy’s mistakes don’t stay internal.
- Incorrect stats damage client confidence
- Follow-up emails quietly undermine credibility
- Calls begin with “Just to clarify the attachment…”
Trust erodes while Andy insists:
“The numbers themselves are right — it’s just the file.”
The file is the problem.
😡 The Internal Meltdown
Andy doesn’t blame IT.
Andy doesn’t blame Outlook.
Andy blames Andy.
Each incident is followed by:
- Head in hands
- Heavy sighs
- Furious self-lecturing
- A vow to “double-check next time”
Next time arrives immediately.
The mistake repeats.
🧠 Additional Aggravating Factors
- Writes “See attached” before attaching anything
- Refuses cloud links because “attachments feel more official”
- Sends correction emails faster than the original
- Asks, “Did it come through?” while visibly sweating
⚖️ Sentence
Andy has been sentenced to:
- Permanent attachment anxiety
- Mandatory pre-send checks
- Removal from any email chain marked URGENT
And one final reminder carved into corporate stone:
If you haven’t attached it, you haven’t sent it.
Frequently Asked Questions (FAQ)
Why do people forget attachments in emails?
Because sending emails becomes automatic. People assume the file is attached, click send too quickly, and only notice when it’s already in someone else’s inbox.
How common is sending the wrong attachment at work?
Very common, especially when people are rushing or multitasking. In Andy’s case, it’s happened 47 officially logged times, with countless near-misses.
Why is sending the wrong file a problem for businesses?
Wrong attachments can damage credibility, confuse clients, and send incorrect or sensitive information externally, which can harm business reputation.
Why do people repeat the same attachment mistake?
Because email is routine and people rely on habit instead of verification. They often only check after sending, when the damage is already done.
How can workplaces reduce attachment errors?
Encourage a final attachment check, prefer secure cloud links when possible, and adopt a simple “paperclip check” rule before sending externally.
