Real Challenges of Claude Code in Coding
Personal experiences & the stuff that actually bites when using Claude Code.
Introduction: The Excitement and the Reality
When I first handed Claude Code an end-to-end feature UI, backend, database migrations it felt like a breakthrough. Tasks that normally stretched across multiple sprints were flying by. Claude scaffolded components, generated routes, wired models, and even spun up tests.
But then, around the 75% mark, the magic started to fade. Errors piled up. Context blurred. Debugging became a chore, not a shortcut. Instead of flying through development, I was knee-deep in manual reverts and cleanup.
And that's the part most people don't talk about: Claude Code is not frictionless.
It's powerful, yes. But it also comes with quirks, frustrations, and very real challenges that can slow you down if you don't prepare for them. These aren't abstract "AI limitations." They're the kinds of issues that waste hours, derail sprints, and frustrate both founders and devs who thought Claude would be an autopilot.
Below are the real-world challenges I've run into and that many others across developer forums have echoed when trying to use Claude Code seriously in production work.
1. Context & Session Overload
Claude's context window is both its greatest strength and its most limiting bottleneck. It can absorb a huge amount of detail at once but once you start piling on feature specs, logs, and code snippets, that window fills up fast.
Even with /compact, the "compacted" context doesn't stay lean for long. After just a few more interactions, the window bloats again. Suddenly Claude forgets instructions you gave 20 minutes ago. You find yourself re-explaining conventions or clarifying file paths that should already be obvious.
Developers everywhere complain about this:
A Reddit user in "Claude Code's tiny context window is driving me insane" vented:
"As soon as it compacts, the context window is immediately 80% full again … It can't get more than a couple of steps before compacting again and losing its place."
Another thread, "Context Anxiety What do you guys do when your Claude Code is almost out of context?", described a workaround where one dev literally ran two parallel Claude sessions: one for deep analysis, another for actual implementation. They bounced between the two like human middleware.
That's not productivity that's duct tape.
In my own case, when working on a feature-rich dashboard, Claude gradually started mixing details from unrelated modules. At one point, it reused an auth snippet in a billing component completely out of place. I realized it had simply lost track of where it was.
👉 Why this matters for founders: If your dev team relies too heavily on a single long session, productivity nosedives. The AI burns cycles reprocessing context instead of shipping code.
The fix? Break work into smaller, context-friendly chunks. Treat sessions like sprint tickets, not marathons. Otherwise, context overload turns your "AI teammate" into a forgetful intern.
2. Debugging, False Fixes & Repetition
This is one of the most frustrating parts of using Claude Code: it gets stuck in loops.
You'll surface a bug, paste logs, and get a fix. But when you rerun, the same error appears. Feed that back to Claude, and it suggests… the same fix again. And again. And again.
It feels like watching someone mash Ctrl+C/V with different variable names.
Real stories:
From the Reddit thread "When Claude 3.7 taps out and you have to debug like it's 2010 again":
"Thought I was being smart by asking Claude to debug it for me … Claude just kept suggesting the same solutions over and over that I had already tried … it was some obscure circular import … I actually had to retrace code line by line."
Another dev asked, "How do you guys fix lots of errors in your code in Claude?" The top advice was: wrap everything in tests and let Claude iterate until the tests pass. But even they admitted, on larger projects, that becomes slow and tedious.
In my experience, Claude has a blind spot when debugging complex interdependencies. It tends to propose "plausible" surface-level fixes without fully tracing root causes. For a simple null pointer? Works fine. For a nasty race condition? It flails.
👉 Why this matters for founders: Claude won't replace deep debugging. Teams still need to roll up their sleeves, add tests, and do the old-fashioned step-through. Otherwise, you'll waste hours chasing repeated "fixes" that never resolve the bug.
3. Losing Unintended Changes / Hallucinations
This one bites harder than most people expect. Sometimes Claude just… touches things it wasn't supposed to.
I've seen it:
- Delete config files it thought were duplicates.
- Modify functions unrelated to the task.
- Create new files with bizarre names:
config.prod.production.main.final.final.js.
And it's not just me. Developers vent constantly about hallucinations:
From "The Real Reason Claude Code Feels Broken (And How I Got It Working Again":
"Everything felt off duplicated files, broken context, janky UI output, and weird hallucinated .prod.production.main.final.final files that made me feel like I was in code purgatory."
It's maddening. You ask for a simple feature tweak, and suddenly you're cleaning up phantom artifacts. Worse, sometimes Claude undoes your earlier instructions rewriting logic you had locked in.
The painful part? You often don't notice until much later. By then, those hallucinated changes have crept into your repo and triggered subtle bugs.
👉 Why this matters for founders: Without strict diff reviews and version control discipline, Claude can silently erode your code quality. You won't even know until production blows up.
The only real safeguard is constant verification. Backups, git hygiene, and careful scanning of diffs are not optional.
4. Performance Variability & Interface Differences
Another overlooked challenge: Claude doesn't behave consistently across environments.
Some developers report that Claude Code's local CLI feels weaker than the web interface. Tasks like debugging produce clearer outputs online than they do locally. Others experience terminal clutter, excessive debug logging, or outright glitches.
Examples:
One Reddit thread described how Claude Code got "stuck in debug mode since an update," vomiting logs endlessly in the terminal until it was basically unusable.
Others note that the CLI sometimes feels slower to respond compared to web, particularly on large projects.
In my own use, I noticed that the same prompt produced a cleaner, better-structured answer on the web than in the terminal. It's not catastrophic, but it's disorienting why should the same tool behave differently in different wrappers?
👉 Why this matters for founders: Your dev team's experience with Claude Code can vary wildly depending on how they interface with it. If half the team uses CLI and half uses web, you'll get inconsistent workflows, results, and even trust levels in the tool.
Standardize on one environment. And expect occasional slowdowns or quirks it's not as polished as traditional dev tools.
Conclusion: Lessons Learned
Here's the reality: Claude Code is not broken. But it's not magical either.
The hype makes it sound like you can offload entire features to AI and watch your roadmap shrink overnight. The reality is more nuanced. Claude accelerates development, but it introduces friction of its own.
It struggles with context management forcing you to split tasks into smaller chunks.
It loops during debugging requiring human intervention and strong test coverage.
It creates hallucinated or unintended changes demanding strict diff reviews.
Its performance varies across environments so workflows need to be standardized.
These aren't deal-breakers. But they are real.
For founders, the takeaway is this: Claude Code can be a productivity multiplier, but only if you treat it like a junior dev with extraordinary speed, not like an autopilot engineer. It needs supervision, structure, and guardrails.
If you plan workflows smartly split sessions, enforce version control, write tests, verify outputs you'll get most of the upside without drowning in chaos. Skip those disciplines, and you'll spend more time cleaning up than moving forward.
AI coding isn't "done for you." It's "done with you." And the sooner you internalize that, the faster you can harness Claude Code without being blindsided by its quirks.