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I think it's a good idea. Cert prices vary, and there are reasons for it, and companies would rather pay for stability than save money.

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But you are not paying for a service, because funding OpenSSL is a classic free rider problem: the company would be better of not funding OpenSSL, even though all companies would be better off if they all funded OpenSSL.

By that logic, the tax accountant could argue that they should arrange a company's finances so they pay more tax, in order to pay for more "stability" by funding the government.

Does it matter about everyone else though? Your company values rock solid encrypted communication and it willing to pay a premium to ensure this it remains rock solid. The fact that everyone gets it is just a side effect of that.

implicit in the free rider problem is that the monetary value of your contribution is less than what you gain.

In this case, I think it's safe to assume that a $200 contribution to OpenSSL won't repay the contributing company $200 of improvements.

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