The Association received a severe shock in 1882 by the failure of the Scottish Security Company, which the Association had invested the funds of the Ladies’ Bursary. In consequence of that the competition ceased for many years until, in 1898, by dint of much individual collecting, the Bursary was resumed.

A further compliment was paid to the Association in 1887 by the Caithness men settled in San Francisco asking for a copy of the Edinburgh Caithness Association’s Rules in order that they might model upon them the Rules of their proposed Society.

On 19th August 1887 the Association celebrated its jubilee by dining in the Station Hotel, Wick. Seventy-seven gentlemen (none of the ladies exercised their rights as members) were present under the Chairmanship of the Earl of Caithness, and the croupiership of Provost Riach, fifty of them inscribing their autographs in the Minute Book of the Association.  When, ten years later, the Association proposed to celebrate its sixtieth anniversary it was doomed to disappointment. To mark that milestone of its journey the directors had decided on a reception in Edinburgh, on a date to suit the convenience of the Duke of Portland, who had on the death of the Earl of Caithness in 1889 been elected President.  The Association could not draw from their funds the money required to meet the expenses of the reception which was to amount to £60, and as the individual subscriptions realised only £25 the idea had to be abandoned.

The members were, it will be observed, not over given to social relaxation in their corporate capacity, they attended to the matters which were entrusted to their care and had the satisfaction of seeing all their bursaries but one attain to some degree of prosperity.  The Rev. Dr. Alexander Miller of Buckie, had in 1889 given £100, which he later increased to £220, for a bursary (in addition to smaller sums meant as contributions to replace the lapsed Ladies’ Bursary) the first of which “Miller Bursaries” was awarded in 1893.  The year 1889 also saw the re-commencement of the school prize and bursary competitions which had been in abeyance for several years.