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Original Timeline we know that following the landings in southern Italy, in September 1943, the Western Allies proceeded up the Italian peninsula until they ran into the German 'winter line'. Here they stopped whilst Monty reorganized and prepared, and then in early December, 1943, with a 'lot of luck' and some brilliant deception operations (and some classic directives from Hitler), the Western Allies under Monty forced the lines, 'bagged' most of the German army which had been opposing them, and were in Rome by Christmas. The Germans threw more troops into Northern Italy, to garrison the 'Gothic Line', but Allied deception operations convinced them that landings in northern France/the Low Countries/Norway were the major threat, and they didn't have enough to stop the Western Allies from breaking the Gothic Line at the end of April/start of May, and cleaning out most of what was left of Italy. Then, in June 1944, the Western Allies moved along the coast with a series of amphibious hooks into southern France, soon had Marseilles, and were ready to drive up the Rhone Valley.

What if the Italian campaign comes to a halt though, maybe running up against the Winter Line and sticking there for half a year or more? Maybe the Germans get lucky and drop a stray bomb on Monty, or Hitler doesn't tell his generals exactly where the W. Allies will attack and how, and get it so spectacularly wrong. And without ongoing success in Italy, and with the presidential elections looming, Roosevelt issues an ultimatum to Churchill of no more troops for Italy, and instead (to keep their promises to Stalin of a front in France by mid-1944) they have to go cross-Channel (i.e. carry out 'Operation Overlord' for real)? How would a W. Allied attempt to land in Northern France or the Low Countries go in mid-1944? Besides all the concrete and steel he had Rommel pouring into building the 'Atlantic Wall', Hitler had all the ports garrisoned like crazy and the disastrous Dieppe raid in 1942 showed just how bloody any attempt to take a port by direct assault from the sea could get. :( And without a port, could the W. Allies have landed in anything like enough strength to achieve very much of meaning, without the capacity to keep a serious sized army in supply or to get to it heavy equipment in any volume? (Good luck putting ashore a Pershing tank in 1944 without a port!)
Of course, part of the OTL timeline deception operations which convinced Hitler to pour more and more troops into the area along the Channel coast in early 1944 were stories relayed to him via double-agents that the W. Allies were going to take 'floating harbours' with them, when they invaded; could such things have actually been built and have worked (and survived in the Channel environment - the weather in the early summer in 1944 had some pretty brutal storms, after all)?
And how much arm-twisting would it have taken on Roosevelt's part to get Churchill to actually green-light a cross-Channel operation? In his post-war memoirs Churchill wrote fairly frankly that he was adverse to the idea of such an 'adventure', and that he wanted the focus to stay on the front (in the Mediterranean) where the W. Allies were already 'ashore' in mainland Europe, because he feared a 'Gallipoli, on a vastly larger scale', should the Allies try to cross the Channel to force a landing on the coast of Northern France.

Edit:
I suppose what it comes down to is that if the Italian offensive 'gums up' to the point that the W. Allies can't support/make a move across the border/along the coast into Southern France, in mid-1944, then:
1) Could the W. Allies actually breech the lines of bunkers, walls, naval mines, and various beach-obstacles in Northern France and put ashore a force in the face of German resistance?
2) Assuming a force could be got ashore and German immediate counter-attacks suppressed with a combination of naval gunfire and (if close enough) airpower flying from southern England could it be kept in sufficiently good supply (with equipment, ammunition, food, fuel, and other stuff) to do anything other than sit there on the beaches without a 'real' port (such as Cherbourg, Calais, Le Havre, etc)?
3) Could/would Churchill be persuaded to go along with such a scheme in the first place, in despite of the first two problems, outlined above, that any such operation would stumble (and perhaps fail) against?

NB
For the confused, see the wiki on 'DBWI': http://wiki.alternatehistory.com/doku.php/alternate_history/double_blind_what_if?s
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