I have a remote server that only allows logins through a browser https request. I want to download images from it, and cache them and use them in a local job. What are the security risks with automating this job using the python requests library assuming the local server is secure and stores the password securely?
Your question is kind of vague as written, but...
I have a remote server that only allows logins through a browser https request.
Er. Basic or digest authentication, I assume? Or Windows integrated security, if you're using IIS?
Assuming that you're just pulling down images from some kind of password-protected web server location via standard HTTPS, the biggest risk I can see is the credentials. You would mainly be risking unauthorized people viewing the images, or maybe someone replacing the images with something malicious if the server is compromised.
(Unless you mean "images" as in "executables" that you download and execute. Then more the second thing.)
But it's possible that I don't fully understand the question.