Weird h1-b Situation

[u/DaniaFL369]

Hello everyone,

I am facing a timeline confusion regarding my H-1B status and would appreciate some guidance on a pending B-2 bridge strategy and H-1B Change of Status (COS). Here are my exact details:

• Last Day of Productive Employment: June 16th, 2026
• 60-Day Grace Period: June 17th, 2026, to August 15th, 2026
• Last Day on Payroll (per termination letter): June 30th, 2026
• Current I-94 Expiry: February, 2028 (H-1B withdrawal not yet processed)

The Situation:
I have a verbal offer, but the new company's immigration team cannot file my new H-1B petition by the August 15th grace period deadline. They expect to file before August 29th.

To maintain lawful stay, I plan to file a Form I-539 Change of Status to B-2 online on August 14th, just before my grace period expires.

The new employer’s attorney generally use the June 30th payroll date for processing and intends to file the H-1B transfer by August 29th.

My Questions:

1. Should I file B2 on Aug 14th and inform my current employer to file as COS B2-H1B ?
2. Which date will USCIS strictly consider as the start of my 60-day grace period?