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For example, the American operation name for the assault on Okinawa was known as Operation Iceberg. However, Okinawa is a relatively hot area of Japan, and as far as I know, there were no icebergs or snow anywhere close to there, not even in that season.
So based off of that example, do military operation names ever have any correlation to the op itself? Does the name itself convey any meaning? Or do they just pick a random word to describe it?
Good military operation names are picked for these reasons: to deliberately deceive the enemy, to have no association with the operation whatsoever, to raise the morale of the troops, or for political/marketing reasons.
The US is big on giving high level operations that will be announced to the public impressive names like "Desert Shield", "Desert Storm", "Desert Sabre" and "Just Cause". These are operations that are already intended to be discussed in public. The names are picked so the press isn't talking about "Operation Blue Spoon" (the original name for Just Cause). They usually contain many, many lower level operations with more secure names.
Operation Vittles was the name for the US airlift of supplies to West Berlin during the blockade. Operation REFORGER is an acronym for "REturn of Forces to GERmany" and it's also symbolic of the intention to reforge the German army in the event of a Soviet attack. Operation Magic Carpet returned US troops to the US after WWII. Operation Eagle Claw would have had US special forces snatch US hostages out of Iran using helicopters (it was a disaster). And so on.
The British military, more secretive and devious than most, called their operations in the Gulf War Operation Granby which is the name of a British commander in the Seven Years War and has nothing to do with Iraq. Again in 2003, what the US called Operation Iraqi Freedom the British called Operation Telic, and the Australians called Operation Falconer. During WWII Prime Minster Churchill would regularly tinker with operation names (and everything else) he thought might give something away.
If you look at the list of Japanese operations, they give a lot away in their operations. Operation AL is an attack on Alaska and Aleutian Islands, Operation MO is on Port Moresby, Operation MI is on Midway, etc. These names were likely picked for expediency during early planning and never changed.
The invasion of Normandy was originally Operation Slegehammer. The lesser known invasion of southern France was Operation Anvil to match. They were changed to Overlord and Dragoon to avoid any information leaking out. (D-Day was Operation Neptune).
Going the deception route, the German invasion of Denmark and Norway, very much intended as a surprise, was called Unternehmen Weserübung or Operation Weser Exercise implying an exercise on the Weser river nowhere near Norway. As this was during the Phoney War or Sitzkreig period, the "exercise" part fed into the Allied perception that the Germans weren't going to attack. Later, Germany would do the same thing with Unternehmen Wacht am Rhein or Operation Watch on the Rhine implying a plan to defend the Rhine River which is exactly what the Allies expected; this was the code name for The Battle Of The Bulge.
If you want to know more, this article from Parameters goes into some detail about military naming choices. You can also pick through this list of military operations and find plenty of examples, though keep in mind that list is likely to contain more high level and popular operations which are more likely to be political branding.
Late to the party as usual . . . but as found in the documents available from the George C Marshall Library-Foundation (https://www.marshallfoundation.org/library/results/?fwp_format=2), Winston Churchill, indeed, wrote on the subject of code names. In a memorandum of 8 August 1943 he wrote to General H. L. Ismay, his chief military assistant, evidently in response to a listing of code names:
1. I have crossed out on the attached paper (marked A) a large number of unsuitable names. Operations in which large numbers of men may lose their lives ought not to be described by code-words which imply a boastful and over-confident sentiment such as “TRIUMPHANT”, or conversely which are calculated to invest the plan with an air of despondence, such as “WOEBETIDE”, “MASSACRE”, “JUMBLE”, “TROUBLE”, “FIDGET”, “FLIMSEY”, “PATHETIC”, and “JAUNDICE”. They ought not be names of a frivolous character, such as “BUNNYHUG”, “BILLLINGSGATE”, “APERITIF”, and “BALLYHOO”. They should not be ordinary words often used in other connections, such as “FLOOD”, “SMOOTH”, “SUDDEN”, “SUPREME”, “FULLFORCE”, and “FULLSPEED”. Names of living people or Ministers or Commanders should be avoided, e.g. “BRACKEN”.
2. After all, the world is wide, and intelligent thought will readily supply an unlimited number of well-sounding names which do not suggest the character pf the operation or disparage it in any way and do not enable some widow or mother to say her son was killed in an operation called “BUNNYHUG” or “BALLYHOO”.
3. Proper names are good in this field. The heroes of antiquity, figures from Greek and Roman mythology, the constellations and stars, famous racehorses, names of British and American war heroes could be used, provided they fall within the rules above. There are no doubt many other themes that could be suggested.
4. Care should be taken in all this process. An efficient and a successful administration manifests itself equally in small as in great matters.
W.S.C.
8.8.43
On 23 September 1943, Leslie Rowan, Churchill”s private secretary. sent the above to Lt. Col. Frank McCarthy of General George Marshall”s staff in Washington under this cover:
Dear Frank,
Herewith are the Prime Minister’s minute about code names and the list of code names which he promised to send to General Marshall. As I told you, I could not let you have this at Washington because we had not the list available.
Thank you very much for your kindness at Washington, and especially for the dinner party. I hope that I shall be able to return your hospitality.
Yours
Leslie Rowan
General Marshall responded to the Prime Minister on 1 October 1943:
Dear Mr. Prime Minister:
I received your minute to General Ismay on code names and took the matter up immediately with our Joint Security Control.
All are in agreement with your views. In the future, the names recommended for projected operations will be selected in accordance with the principles which you outlined.
Faithfully yours,
G. C. Marshall
The list of code names, with strikethroughs can be found here https://www.marshallfoundation.org/library/wp-content/uploads/sites/16/2015/03/43.09.23-Code-Names-3_opt.pdf
And this, from 1 September 1943, might be interesting: https://www.marshallfoundation.org/library/digital-archive/memorandum-for-the-assistant-chief-of-staff-g-2-strong-assistant-chief-of-staff-opd-handy/
Yes, most certainly (though not always) - consider Market Garden in September 1944. Market was the airborne drop to take the cities and bridges, and Garden was the relief operation by British XXX Corps spear-headed by the Guards Armoured Division.
The British had a penchant for two word operational names, and in this case the two names were easy to keep distinct in planner's minds, while not hinting at Arnhem directly.
Another example is Operation Neptune as part of Overlord: the Normandy Invasion of June 1044. Surely the name of the Roman King Under the Sea is an apt name for the largest (or second largest, depending how you count Kublai's invasion of Japan) amphibious invasion in history, and Overlord seems also apt for the encompassing operation that included the airborne and logistics elements of the invasion as well.
Part of the point of these codenames is so that if enemy intelligence gets hold of some of the chatter about the operation, it isn't immediately obvious what the exact objective is. So ideally, yes the names will be completely random.
Up until about 30 years ago the U.S. military would assign random code names for exercises, landings, headquarters, attack plans and other schemes. During World War II, Prime Minister Churchill urged leaders to come up with valiant names for battles so no mother of a fallen soldier would have to be told her son was killed “in an operation called ‘Bunnyhug’ or ‘Ballyhoo.' The point was to protect secrecy to not afiliate a geographic location or specific feature to a region being invaded; to confuse the enemy and simplify communications. Ever since, high-profile U.S. combat campaigns get rousing names that not only are used for funding requests to Congress for medals and campaign ribbons. They also attempt to shape public perceptions. In other words they operate as a form of propaganda. U.S. troops in Vietnam were also were sent on lethal missions named Flip Flop, Hopscotch and Jingle Bells among other embarrassing titles
Operation Papercliphad significance.