iA Writer vs Guessly: Which Should You Choose in 2026?
Choosing between iA Writer and Guessly 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:
iA Writer
The benchmark Markdown writing app designed for focused, distraction-free writing.
Best for you if:
- • You want the higher-rated option (8.0/10 vs 7.6/10)
- • You need writing apps features specifically
- • Distraction-free Markdown writing environment with Focus Mode.
- • Advanced editor tools like Syntax Highlight and Style Check for improving writing quality.
Guessly
Daily riddles for brain training and fun.
Best for you if:
- • You need something completely free
- • You need habit tracking features specifically
- • Offers daily riddles for brain training.
- • Focuses on cognitive skill improvement.
| At a Glance |  Guessly | |
|---|---|---|
Price | Paid | Free |
Best For | Writing Apps | Habit Tracking |
Rating | 80/100 | 76/100 |
| Feature | iA Writer | Guessly |
|---|---|---|
| Pricing Model | Paid | Free |
| Editorial Score | 80 | 76 |
| Community Rating | No ratings yet | No ratings yet |
| Total Reviews | 0 | 0 |
| Community Upvotes | 0 | 0 |
| Categories | Writing AppsGrammar & Style | Habit TrackingFocus & Pomodoro |
Understanding the Differences
Both iA Writer and Guessly solve similar problems, but they approach them differently.iA Writer positions itself as "the benchmark markdown writing app designed for focused, distraction-free writing." while Guesslyfocuses on "daily riddles for brain training and fun.". These differences matter depending on what you're trying to accomplish.
When to Choose iA Writer
iA Writer makes sense if you're looking for a comprehensive paid solution. With a score of 80/100, it's our top pick in this comparison.
When to Choose Guessly
Guessly is worth considering if you need a free tool.
Who Should Use What?
Bootstrapped or small team?
Guessly won't cost you anything to start, which is exactly what early-stage teams need.
We'd pick: Guessly
Growing fast?
Your team doubled last quarter and you need tools that won't break when you add 50 more people. iA Writer handles scale better in our testing.
We'd pick: iA Writer
Enterprise with complex needs?
You need SSO, compliance certifications, and a support team that picks up the phone. iA Writer is built for organizations like yours.
We'd pick: iA Writer
Still not sure? Answer these 3 questions
How much can you spend?
Zero budget? Guessly won't cost you anything.
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 iA Writer higher (80/100). But the community has upvoted Guessly more (0 votes). Pick your source of truth.
Key Takeaways
What iA Writer Does Better
- Higher overall score (80/100)
- Our recommendation for most use cases
Consider Guessly 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 iA Writer (80/100). But the honest answer is that "better" depends on your situation. iA Writer scores higher in our analysis, but Guessly 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 iA Writer or Guessly better?
Based on our analysis, iA Writer scores higher with 80/100. iA Writer ispaid while Guessly 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 iA Writer to Guessly 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 iA Writer and Guessly offer free trials?
Most software in this category offers free trials or free tiers. iA Writer is paid with potential trial.Guessly is completely free. Visit their websites for current trial offers.