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Regarding the entry in the Dictionary of Vexillology for "Insurance Flag":
"The term for a 19th Century flag, now obsolete, usually showing a vessel’s insurance number and issued by the appropriate marine insurance company, association for mutual insurance or similar – a number flag. Please note that this is not an established term, but has been introduced by the Editors since no contemporary source describing such flags could be found."

A vague reference to an insurance flag was made in Lowestoft Magistrates' Court on 22nd July 1885. H.J. Sandwell, Master of the trawler 'Sea Flower' LT 566, was charged with concealing the nationality of his ship by flying a Dutch flag. Sandwell claimed that he did not know that it was the Dutch flag. Red, white and blue were English colours and the flag had been hoisted as a signal to the four other trawlers accompanying him that he was raising steam and would be hauling in his trawl in one hour. The only other flags on board were a burgee and the flag of the club in which the ship was insured.
[National Archives (PRO) MT 10/432]
David Prothero, 3 February 2009

I am not sure if this was indeed the "insurance flag" as meant in the Dictionary of Vexillology or was it simply a flag of the club (insurance here mentioned being incidentally), but I have no idea what was the 1885 practice there.

What is meant to be covered by the Dictionary of Vexillology entry (as far as I understand it) are those flags (cf. the alternate term "number flag") used for example in Austria-Hungary and some other European countries, to be hoisted atop of a mast containing a large number of the ships "registration" or insurance number (whatever it was actually called). In many 19th century paints of various ships (a popular art discipline in 19th century) these flags are clearly visible. As far as I have noticed, these were monocoloured flags with large two or three cypher numerals. I have seen the flag being blue, red or white, with white letters in the first two cases and blue in the last. I suspect that the colours may have something to do with the port of registration (or some other such rule, maybe the insurance house), since it appears that the ships of the same owner used the same colour pattern for those flags.
Cf. http://www.ppmhp.hr/files/24-1004-full.html the blue flags on the foremasts (also note the onomasts on the main).

I have not found any literature regarding these number flags and they are largely a mystery to me, however, it seems that they appear regularly on the Austrian-Hungarian ships of 19th century.
Željko Heimer, 6 February 2009

I expect the "early 19th century" might be a bit local. We have the painting of De Groninger Eendracht showing it flying the number/registration flag of the compact Orange, before being wrecked on Lundy in 1942. That's considerably later than the early 19th century.

These flags had to be simple, but Orange, for example, used an orange field with a Dutch Canton, Zeemanshoop used an anchor in the canton, several merely wrote the numbers in the white stripe of a tribar, etc. I guess the colleges might have used more elaborate flags than the compacts.

Compacts were usually local organisations. Insurance elsewhere probably was little different. The organisation's choice of colour would often be inspired by the local flag, if any, but could be different, as the reference to the Royal House of Orange demonstrates.

See the Zeemanscolleges page for the colleges, and the introduction there plus the notes on Orange on for the compacts. "Insurance flag" might be a bit limited, as it excludes the colleges, and probably similar organisations elsewhere. Obviously, as the insured with the compacts were "flag members", the flags will have been "member flags". I don't know whether insurances elsewhere were mutual as well, or whether they would have had a different form of registration.
Peter Hans van den Muijzenberg, 21 February 2009

There is a good article in [dsa] by Johhan Schmidt "Signal- oder Nummernflaggen", Deutsches Schiffahrtsarchiv 6 (1983) pp. 265–271.
http://ww2.dsm.museum/DSA/DSA06_1983_265271_Schmidt.pdf

Apparently, these insurance flags were introduced indeed after the initiative of the insurance companies to more easily track and identify individual ships. They seem to appear in 1820 in the Netherlands and by the mid-19 c. spread through Germany (and presumably other countries, we know that Austria[-Hungary] used them as well).

It appears that by the mid-second half of the 19th century these insurance flags were replaced with 4 numeral flags of the International Signal Code ("Marryat"), although apparently that was not everywhere implemented at once.
Željko Heimer, 7 July 2017