Currently, my site is dynamically creating images with watermarks and then uploading these to amazon s3, with details being saved to a MySql table.

What would be the best way to perform this action for all images that I want to upload. There are approx 19,000 images within the database which need uploading. Could I handle this with a scheduled event to run every 30 minutes to take the first 100 and upload those? Would this timeout?

I am using SQL Server  2016 (32 bit and 64 bit)