Missing the biggest red flag of all, engineers wanting to just play with new toys and pad their CVs. Ask the engineers why they want to rebuild and listen carefully to the answer and if it’s vague handwaving and buzzwords (microservices! Containers! New JS framework!) and no hard numbers to justify it, just say no.
For example “we spend X/year on AWS but if we spend Y to rewrite in C++ we need fewer VMs and can cut that to Z/year” is simple calculations. If your engineers can’t even do that, their motives are suspect.
On the other hand, “we cannot hire anyone to work in COBOL/Perl 5.8/Tcl/other outdated language” is a very real problem. It turns out that 2018, developers are judged for working too long in old technologies even when we know as in industry that a developer can learn a new language.
For example “we spend X/year on AWS but if we spend Y to rewrite in C++ we need fewer VMs and can cut that to Z/year” is simple calculations. If your engineers can’t even do that, their motives are suspect.