Neither the Canadian firm nor its Canadian bank were familiar with IRA accounts but acknowledged the need to follow instructions on account names and chain of custody. The firm agreed to accept brokerage checks (Roth & Traditional) issued to me but endorsed over to the company. Unfortunately their bank did not accept the 3rd party endorsed checks, leaving me with few options and the deadline already technically past.

I explained the situation to my brokerage and reiterated the overall transaction objectives, but random (800) number customer service reps are no guarantee of expertise or commitment to problem solving. My request for wire transfers payable to the stock issuing firm was again rebuffed, so per their suggestion I had the two transfers (Roth & Trad) wired to my credit union. From which I made two corresponding same-day wire transfers to the Canadian bank, properly annotated to match the Roth and Traditional share subscriptions.

The next complications arose when I received the ensuing transaction confirmations:
a) Contrary to written assurances from the issuer’s accounting firm, the awarded warrants were in paper (PDF file) format only and lacked a CUSIP number, hence could not be held in my brokerage account until exercised for shares following the 18-month hold restriction.
b) The awarded shares, held by Computershare (transfer agent), could not be accepted by my brokerage for transfer until after the 4-month hold expired.

Not wanting this transaction to go off the rails, I uploaded a detailed letter with attachments to my brokerage notifying them of the delay and requesting confirmation that the shares would be accepted for transfer into the two IRA accounts when restrictions were lifted. And advising them that since the warrants were non-tradable, I would arrange to hold them separately in SDIRA accounts.