fakewokesnowflake's journey

I started a new job at a small company in mid-April, leaving behind a medium-sized firm where I would miss out on my annual bonus. To make up for this, the new company included a 10% sign-on bonus in my contract, payable after my first full month of employment. However, when May rolled around, I didn’t receive the bonus. I thought maybe it was due to the timing, so I waited another pay period. By June, still no bonus, so I approached the CEO, who mentioned they were discussing whether I wanted the bonus all at once or spaced out for tax reasons. I opted for the lump sum. When the next pay period came, the bonus was still absent. After expressing my frustration, the CEO assured me they would check with the COO and rectify the payroll issue. They claimed it was an oversight due to their automated system. The following pay period came and went without the bonus, leading to another conversation where the CEO promised a special payroll run to ensure I received it. Now, it's Tuesday, and I can see they didn’t run that special payroll. I’m feeling really frustrated because it’s been months since I was promised this bonus. I genuinely like the company and my role, but I’m worried that pushing the issue further might create tension. I’m unsure of my next steps. Should I escalate this or try to resolve it more casually? I’m also starting to wonder if I should begin looking for other opportunities.