"separating" flight tickets (helsinki-damascus-tel aviv-helsinki)

However, we asked the local Ebookers agency (the cheapest tickets we’ve found so far) if they could split the ticket, so that we could first print the ticket to Damascus and only print the return when we are in Israel.

That won't work. Traditional paper tickets have fare calculations on them that make the full flight iternerary obvious. Even electronic tickets often have these on them. Furthermore the full itinerary of any given booking code is shown in full when the code i entered at check-in. I.e. you really need two seperate tickets.

They claimed the tickets cannot be separated if we want to buy a round-trip, which is of course much cheaper than two individual flights.

This indeed is true. If the relevant tariff only allows for round trip flights, the itinerary cannot be split up into two different bookings (at least not by ordinary booking agents). However many airlines have done away with premiums/extra charges for one-way flights : check if this is the case with your particular airline by double-checking prices via one of the internet flight booking engines.

I had the same problem when my parents flew into Saudi Arabia and out of Israel on the same ticket (and flew a one way from Saudi to Jordan, and entered Israel from there). When they applied for the Saudi visa, they needed to show flights into and out of Saudi. It was an e-ticket booked online, so I doctored the email to show a flight into and out of Saudi. Embassy staff didn't know the difference! They also had (but were never asked to show it) at immigration the same doctored itinerary when they got to Saudi.

You claim immigration in Manchester knew you were returning a different way without showing them the printout of your ticket, which is something I never considered. I wonder whether immigration just chose not to make a fuss, or if they didn't have that information available to them. Oh well, just lucky I guess.

George 5 said part of it is that they see the info at check-in, but since they flew a separate itinerary from Saudi to Jordan, they wouldn't have noticed it because it was a different ticket. I think you will be making your way by land, so the same case could apply to you as it did to my parents.

Syrian authorities are just as relaxed as everybody in Syria, they're not paranoid like the USA or UK!

I'm pretty sure they'll just check your visa and passport and don't care about your ticket.

If you want to be 100% sure about the succes of your trip I recommend the following:

Book a HEL-DAM//CAI-HEL open-jaw ticket instead of TLV-HEL. It might be even cheaper, but for sure not much more expensive!

Getting from Israel to Cairo by bus takes about 1 day.

I forgot to add : Your main concern is the airline, as immigration in Syria in all likelyhood will not want to see your tickets. Most western airlines won't care if you fly out of Tel Aviv.
I.e. the only case in which all of this is of practical importance is if the flight to Syria is with Syrian Airlines or another airline from a country that bars travel to Israel. Note also that some airlines (e.g. Austrian from Vienna) code-share with Syrian Air, in that case you might also run into problems.

Thanks so much for all the replies and suggestions! They are appreciated. The best deal we have found is with Czech Airlines through Prague, so it looks like this is not going to be a problem after all. I guess we'll be fine if the immigration officials don't ask to see the tickets.

So, thanks again, and I'll probably come back with more questions once our plans become a bit more concrete.