Is transit visa required for my journey via Reykjavik (KEF) where there is a date change during transitioning

Question

I have booked a round trip flight ticket of Wow Air which is via Reykjavik (KEF) airport. My layover details are below:

New Delhi -> Toronto    (2 hrs Layover at  Reykjavik  )
Toronto -> New Delhi    (7 hrs Layover at  Reykjavik  ) 

My concern is with the return ticket transit visa requirements (if any). I have read in Iceland visa sites and forums that

"Visa required, except for Holders of confirmed onward tickets transiting on the same calendar day"

My Ticket details are below. There will be a date change while transitioning in my onward ticket in the late night flight. Will it create any issue for me: I am an Indian Citizen and Canada PR? Do i need a transit Visa for any part of Journey? Please help.

Departure:
Fri, Mar 22, 2019
New Delhi (DEL) 07:00Toronto (YYZ) 18:00
Flight 1: | 11h 50m | WW323 | Operated by: WOW air
Layover: 2h 10m | Reykjavik (KEF)
Flight 2: | 6h 30m | WW213 | Operated by: WOW air  

Return:
Wed, Mar 27, 2019
Toronto (YYZ) 19:00New Delhi (DEL) 03:15 + 2 day
Flight 1: | 5h 45m | WW214 | Operated by: WOW air
Layover: 6h 55m | Reykjavik (KEF)
Flight 2: | 10h 5m | WW322 | Operated by: WOW air

Answer 1

You can use the Transit without Visa (TWOV) facility in Rekyjavik as you will transit Iceland on the same calendar day for both of your flight legs.

You have not posted the actual arrival and departure times of the flights but given the flight numbers it is easy to find them on the internet. The DEL-KEF legs are on soon to be launched flights of Wow Air so the schedule is (somewhat) tentative. Your complete itinerary as far as I could gather is as follows:

Onwards Flights:

• DEL-KEF on WW323 - Depart 0700, Arrive 1320 (Local Times)
• KEF-YYZ on WW213 - Depart 1530, Arrive 1800 (Local Times)

As you can see you have a 2h10m layover at KEF on the same day so you should be fine as per the Timatic advice you have posted

Return Flights:

• YYZ-KEF on WW214 - Depart 1900, Arrive 0445 (Next day)
• KEF-DEL on WW322 - Depart 1145, Arrive 0315 (Next day)

On your return flight you will be in KEF between 0445 and 1145 of the same day. Even though your flights span 2 days (between departure from YYZ and arrival at DEL), for purpose of transit you are only in KEF for 7 hours on the same calendar day.

Entering your residency and citizenship information on Timatic tells us

TWOV (Transit Without Visa): Passengers arriving from a non-Schengen Member State with a confirmed onward ticket for a flight on the same calendar day to a third country which is not a Schengen Member State. They must:

• stay in the international transit area of the airport, and

• have documents required for the next destination.

So you should be fine to transit KEF without a visa for onward and return journeys as long as your luggage is checked through.