How do Sky know if you have both Digiboxes connected to one phone line?
Sky can send a signal via satellite to tell each Digibox to "phone home". Sky's computer can see the phone number and the serial number of each Digibox. (If your phone number is normally withheld you must enter the 1470 prefix in the menu of each Digibox! and remember to use phone filters if you have broadband)
Sky insist that you have both Digiboxes connected to one phone line to stop you from lending your Digibox and mirror card to someone else who ought to be paying the full subscription.
How often do Sky check this?
Nobody knows for certain but my guess is: about once a month.
If it's difficult to add an extra hard wired phone socket for your second sky box there is a kit which plugs into the mains socket and sends the phone connection through your 230 volt house wiring.
So can you take your Digibox and card on holiday without Sky finding out?
Only if it doesn't coincide with Sky's monthly (?) check. If they find your Digibox is not connected, they will send you a warning letter. If they find it's not connected a second time, they'll probably invoice you for TWO full subscriptions, backdated to the day you signed the contract.
However, it may be feasible for you to leave both Digiboxes connected at home and take a different Digibox on holiday with one of your viewing cards. You would then be able to watch only the non-premium channels.
There is, of course, a good argument for NOT leaving anything plugged in while you are away from home. The Fire Brigade and the Police recommend unplugging everything, on the grounds of safety. Unfortunately, Sky's lawyers would probably eat you for breakfast
If you are (for example) upgrading a standard Digibox to Sky+ at the same time then your existing card MUST be activated in the NEW Digibox and the multiroom card MUST be put in the existing Digibox. If you do it any other way, the Sky computer system gets confused!