What is the best way to persuade a security manager to upgrade poorly outdated software/devices?

5 pts.
Tags:
Hardware
Security management
Software upgrades
I've mentioned security risk, not to mention how upgrading will do a world of good and provide more features to allow us to enhance our tools to make us more productive. I come from an ISP where IT was not a cost center. I may be spoiled, but we are running on Hoary, and everything is manual it seems. I want to develop - but can't due to the outdates server OS and limitations beyond my control. I need a way to actually convince them that the cost of upgrading is well worth it. Please refrain from "break it beyond repair" I've thought of that - but it's not a very good way to build rapport with my peers :)

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Best way is to jot down the vulnerabilities, risks and threats involved, classifying them in major/minor, and what would be their implications on your setup, security, and business. If Security manager is not convinced still, prove it by actual figures happening in the organization due to these outdated software/ devices.

If still this exercise does not open the eyes of Security Manager, he does not deserve to be a Security Manager as he does not understand the implications and intricacies involved with threats, risks and vulnerabilities.

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