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Retirement extension/reentry permit


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Hi all, can use some clarification on retirement extension/reentry permit, yes, inquired at immigration, (3 officers) none the wiser.      Long version....

I am on a retirement extension that expires then renewed on 24/05 annually. I usually renew approx one month before , at the end of April.

I intend to apply again this coming april  ,and, to also obtain a reentry permit for the following year dated 24/05/2020 to 24/05/2021.    (Q1.) If successful, can i then exit on the 10/05/2020 on on the current extension for that year dated dated 24/05/2019 to 24/05/2020. with no current reentry permit for that year dated 24/05/2019 to 24/05/2020..(or do i need one) returning four months later on my then current retirement extension and reentry permit stamp dated 24/05/2020 to 24/05/2021.. (Q2) do i even need a reentry permit as i will have a valid unused retirement extension stamp in my passport..... Not sure how it works.

 There must be quite a number of tv members traveling under similar conditions,,, would appreciate any feedback... Thanks for your help....

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