The first week back after end-of-year holidays is notorious for IT teams. Even in very mature environments, the same user-driven problems appear every January.
Here are the most common challenges — and why they hit all at once.
1. Forgotten passwords & account lockouts 🔐
What happens
- Users haven’t logged in for 1–2 weeks.
- Passwords expired during the break.
- MFA apps changed phones or were deleted.
Symptoms
- “My password worked before Christmas.”
- Huge spikes in Service Desk tickets at 8:00–10:00 AM Monday.
- Locked AD / Entra ID accounts everywhere.
2. New devices that were never onboarded 💻
What happens
- People got new laptops, phones, tablets as gifts.
- They try to connect personal devices to corporate systems.
Symptoms
- “I got a new iPhone and Outlook won’t sync.”
- Intune / MDM enrollment failures.
- Security teams suddenly seeing unmanaged devices everywhere.
3. VPN, certificate & Wi-Fi failures 🌐
What happens
- VPN certs or profiles expired while people were away.
- Wi-Fi passwords rotated or certificates rolled.
- Routers at home were “upgraded by their cousin.”
Symptoms
- Users stuck at “Connecting…”
- VPN client loops, Wi-Fi authentication errors.
- Mass “I can’t work remotely” tickets at the same time.
4. Outdated devices missing critical updates ⚙️
What happens
- Machines were powered off for weeks.
- Missed Windows / macOS patches, security baseline updates.
Symptoms
- Endless update cycles.
- Compliance failures in Intune / SCCM / JAMF.
- Slow logins, broken apps, BitLocker recovery prompts.
5. Email & Teams issues after security changes 📬
What happens
- IT tightened spam rules or disabled legacy auth over the holidays.
- Old Outlook profiles or cached credentials break.
Symptoms
- “My Outlook keeps asking for my password.”
- Mail not syncing on phones.
- Users convinced IT “broke email.”
6. Access requests forgotten before holidays 🔑
What happens
- Managers promised access “after New Year.”
- Nobody logged the tickets.
Symptoms
- “I can’t access the finance system — I need it today.”
- HR systems, shared drives, ERP access suddenly urgent.
- Escalations because users can’t start work.
7. Leavers, joiners & role changes not processed in time 👥
What happens
- HR changes were queued but not executed.
- Some users left mid-December, but accounts stayed active.
Symptoms
- Former employees still logging in.
- New starters with no equipment or access.
- Compliance & audit concerns immediately after break.
8. Print & scanner meltdowns 🖨️
What happens
- Print servers updated or rebooted.
- Drivers outdated on dormant machines.
Symptoms
- “The printer worked last year.”
- Finance & HR suddenly needing physical documents.
- Queue corruption, missing drivers.
9. Forgotten how things work 🤯
This one is real.
What happens
- Users mentally disconnect from work systems for weeks.
Symptoms
- “How do I log into the VPN again?”
- Surge in basic “how do I…” tickets.
- Training memory wipe effect.
10. Surge volume & ticket pile-ups 📈
Even if every issue is small, they all hit at once.
What happens
- Everyone logs in Monday between 08:00–09:00.
- Helpdesk queue triples before coffee.
Symptoms
- SLA breaches.
- Burned-out Service Desk by Tuesday.
Why this always happens
The holidays create a perfect storm of:
- Expired credentials
- Unpatched systems
- Changed personal devices
- Deferred HR processes
- Forgotten knowledge
All surfacing simultaneously.
Follow me on LinkedIn for more insights on Customer Service and AI.