For most of my work, I worked almost entirely on Linux servers.
Systemd, journalctl, permissions, service files everything felt familiar.
Like many of us, even though everyone starts using Windows first in their life, 95% of real production workloads today run on Linux.
So naturally, I never had a reason to deploy anything as a Windows service… until recently.
And that small requirement turned into a very interesting journey.
🚀 The Challenge: “Can you run this Python/Flask script as a Windows service?”
Simple question, right?
I thought:
“Okay, in Linux I just create a systemd service, set ExecStart, enable the service, and I’m done.”
But Windows?
Windows doesn't have systemd.
Windows has its own entire ecosystem for running background services.
That’s when everything became a learning curve.
🧰 How Services Actually Work in Windows
Windows uses something called the Windows Service Manager.
Instead of systemd units, it uses .exe or scripts wrapped using service wrappers.
To run Python/Flask as a Windows service, I had to understand:
- The Windows Service Control Manager
- How services are registered
- How they start/stop
- Event logs instead of journalctl
- How Python needs a wrapper to run as a service
- How to handle automatic restart, shutdown, timeouts
This felt very different from Linux's clean service file approach.
🐍 The Python Problem: Python is not a Windows service by default
On Linux, running a Python app as a service is simple systemd handles it.
But Windows requires the service to implement specific lifecycle operations (start, stop, restart callbacks).
Python alone cannot directly do this, so we use tools like:
- NSSM (Non-Sucking Service Manager)
- pywin32
- WinSW (Windows Service Wrapper)
These tools create a bridge between Python and the Windows Service Manager.
This step was a major “aha!” moment.
🧪 The Debugging Experience
Another surprise:
Windows services don’t show logs on the console like Linux.
Instead:
- You must check the Event Viewer
- Understand Windows error codes
- Configure stdout/stderr redirection
- Handle permission issues such as “Run as Administrator”
- Deal with locked directories (something Linux rarely does)
My usual habit of tailing logs with:
journalctl -u service-name -f
…did NOT exist here.
It felt like learning another operating system from scratch.
🔄 Auto-restart, recovery, and startup behavior
In Linux, restarting a service is easy:
systemctl restart myapp
In Windows, you must configure:
- Recovery actions
- Startup mode
- Delayed automatic start
- Account permissions
- Environment paths
And yes — Windows treats paths VERY differently.
Another learning curve.
🌐 Network Binding Differences
In Linux, binding a Flask app to:
0.0.0.0
Just works.
In Windows, you might need:
- Firewall rules
- Port permissions
- Service-level access rules
- Administrator privileges
Windows firewall silently blocking your port?
Happens more often than you think.
🎯 What This Experience Taught Me
Even though Linux dominates backend & cloud infrastructure, sometimes you must work on Windows especially for:
- Enterprise environments
- Legacy applications
- On-prem corporate systems
- Windows-native tools
- Financial institutions
- Desktop-based automation
And when that day comes, knowing how Windows services actually work is more valuable than you think.
It reminds you:
“Operating systems are completely different worlds.
And a good DevOps engineer must be comfortable in both.”
🧠 Final Takeaway
This small task “run this Python script as a Windows service” turned into a deep learning opportunity.
I understood:
- How Windows manages services
- How Python integrates with Windows
- How logs, processes, and permissions differ
- Why enterprise systems rely heavily on Windows service wrappers
It was a reminder that even after years in Linux, there’s always something new to learn in another ecosystem.
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