Caddy vs PyPI: Which Should You Choose in 2026?
Choosing between Caddy and PyPI comes down to understanding what each tool does best. This comparison breaks down the key differences so you can make an informed decision based on your specific needs, not marketing claims.
Short on time? Here's the quick answer
We've tested both tools. Here's who should pick what:
Caddy
Modern web server with automatic HTTPS
Best for you if:
- • You need vps & servers features specifically
- • Caddy is a web server with automatic HTTPS and simple configuration
- • It obtains and renews TLS certificates automatically with zero configuration
PyPI
Python Package Index for libraries
Best for you if:
- • You need hosting & deployment features specifically
- • PyPI is the official repository for Python packages
- • It hosts and distributes Python libraries for the community
| At a Glance |  Caddy | |
|---|---|---|
Price | Free | Free |
Best For | VPS & Servers | Hosting & Deployment |
Rating | 88/100 | 88/100 |
| Feature | Caddy | PyPI |
|---|---|---|
| Pricing Model | Free | Free |
| Editorial Score | 88 | 88 |
| Community Rating | No ratings yet | No ratings yet |
| Total Reviews | 0 | 0 |
| Community Upvotes | 0 | 0 |
| Categories | VPS & ServersHosting & Deployment | Hosting & DeploymentAPI Tools |
Understanding the Differences
Both Caddy and PyPI solve similar problems, but they approach them differently.Caddy positions itself as "modern web server with automatic https" while PyPIfocuses on "python package index for libraries". These differences matter depending on what you're trying to accomplish.
When to Choose Caddy
Caddy makes sense if you're looking for a completely free solution.
When to Choose PyPI
PyPI is worth considering if you need a free tool.
Who Should Use What?
Bootstrapped or small team?
When every dollar counts, Caddy lets you get started without pulling out your credit card.
We'd pick: Caddy
Growing fast?
Your team doubled last quarter and you need tools that won't break when you add 50 more people. PyPI is built for teams that are leveling up.
We'd pick: PyPI
Enterprise with complex needs?
You need SSO, compliance certifications, and a support team that picks up the phone. Both have enterprise tiers—compare their security features.
We'd pick: Caddy
Still not sure? Answer these 3 questions
How much can you spend?
Nothing at all? Caddy is completely free.
Do you care what other users think?
Both have similar review counts. Read a few before you commit.
Expert opinion or crowd wisdom?
Our team rated Caddy higher (88/100). But the community has upvoted PyPI more (0 votes). Pick your source of truth.
Key Takeaways
What Caddy Does Better
- Our recommendation for most use cases
Consider PyPI If
- You need a completely free solution
- Its specific features better match your workflow
- You prefer its interface or design approach
The Bottom Line
If we had to pick one, we'd go with Caddy (88/100). But the honest answer is that "better" depends on your situation. Caddy scores higher in our analysis, but PyPI might be the right choice if its specific strengths align with what you need most. Take advantage of free trials to test both before committing.
Frequently Asked Questions
Is Caddy or PyPI better?
Based on our analysis, Caddy scores higher with 88/100. Caddy isfree while PyPI is free. The best choice depends on your specific needs and budget. We recommend testing both with free trials if available.
Can I switch from Caddy to PyPI easily?
Migration difficulty varies. Check if both tools support data export/import in compatible formats. Some tools offer migration assistance or have integration partners who can help with the transition.
Do Caddy and PyPI offer free trials?
Most software in this category offers free trials or free tiers. Caddy is completely free.PyPI is completely free. Visit their websites for current trial offers.