Asset Compilation can fail due to missing dependencies, outdated versions, or path issues. Solution: Precompile assets locally, ensure Node.js & Yarn on Heroku, and add postinstall script to package.json.
Environment Variables errors often result from forgetting to set variables, typos, or not restarting dynos. Solution: Set and verify variables, add debugging checks in initializers, and restart dynos.
Other deployment challenges include Database Setup failures, File Permission issues, and Memory Limits for Asset Compilation. Solutions include running migrations, adjusting permissions, and setting memory limits in Heroku.