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Does anybody think it would be possible to run a DHCP service off a server in the cloud such as Amazon EC2 or a generic VPS? Could it be used in a scenario where the company has many sites geographically speaking (e.g. one DHCP server for many offices spread out throughout the country)?

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Technically, yes. Though a local DHCP server is generally a better choice. DHCP is a pretty "easy" thing, just setting up a old desktop with Linux on it at each site works well, and will be less failure prone that centralizing everything.

If you want to do it, the best way is to connect the sites together via VPN. Either back to a master site, or a node on EC2. Then run a DHCP server on the master site and configure the routers or switches at the other sites to do DHCP forwarding.

If the VPN links or the master site goes down, none of the other sites will be able to pull new addresses. Think carefully about the implications before doing so.

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No this should not be done. DHCP should be running locally. You can generate the config files on one central server, thus administer it from one place.

One (or more) dhcp server should be running at each site.

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You should run DHCP as close to the network as possible. I'd even recommend running it off your switch/router if it has that capability. You need to figure out what it is that you are trying to solve.

If you want machines in one office to communicate with another office by hostname, there are other options. It depends on how your DHCP server and DNS server communicate.

e.g. it is always possible to give out fixed IPs to machines based on their MAC address and have a master hosts file that has those mappings and feed it to your DNS server.

There are other ways that involve more complex configurations between DNS and DHCP servers.

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