I have a tenant that said he mailed rent in July and August for those months but didn't (in writing). He did mail 2 checks in August that he said were for September and October rent. Once I noticed the discrepancy, the missing $1,000, I asked for payment but the tenant said that I noticed too late. I served the 5 day notice as required by Illinois law. The judge basically said that since I accepted checks that were earmarked for September and October that I couldn't use the missed payments for July and August to get forcible entry and detainer but would have to go to small claims for that. Keep in mind that I served the 5 days notice on 10/17 and that $1,000 was due at all times (in real estate, payments get applied to oldest invoices first so the earmarked checks were applied to the missing July and August rents). Since that 5 days notice, the tenant hasn't paid a dime so the total is now at $2650. The judge dismissed without prejudice. Can someone explain what the legal precedent is for what the judge was saying? My lawyer had no clue and I'm still stumped. I now have to redo the entire process starting with a 5 days notice and I don't know if I'm allowed to include the entire $2650 that was legitimately never paid. Thank you in advance.