CRA tax changes for 2026 arrive during the season most Canadians spend actively avoiding the subject. You have a deadline of April 30th. You probably have questions you have not asked yet, because asking means starting, and starting means facing whatever is in the pile.

What does it feel like when the avoidance has gone on long enough that coming back seems impossible? Four or five years of unfiled returns and the weight of it becomes real. The voluntary disclosure program lets taxpayers come forward, clear the record, and walk away without criminal prosecution and with penalties significantly reduced. It exists because the pattern of compounding avoidance is very common.

One senior tax lawyer tested the new CRA chatbot before this conversation. It got the principal residence question completely right. It got the crypto scam loss question completely wrong. Using it well requires already knowing the difference, which is a useful thing to understand before the deadline arrives.

Topics: CRA changes 2026, unfiled tax returns, voluntary disclosure program, CRA chatbot, tax filing Canada

GUEST: David Rotfleisch | http://taxpage.com

Originally aired on 2026-03-10

CRA tax changes for 2026 arrive during the season most Canadians spend actively avoiding the subject. You have a deadline of April 30th. You probably have questions you have not asked yet, because asking means starting, and starting means facing whatever is in the pile.
What does it feel like when the avoidance has gone on long enough that coming back seems impossible? Four or five years of unfiled returns and the weight of it becomes real. The voluntary disclosure program lets taxpayers come forward, clear the record, and walk away without criminal prosecution and with penalties significantly reduced. It exists because the pattern of compounding avoidance is very common.
One senior tax lawyer tested the new CRA chatbot before this conversation. It got the principal residence question completely right. It got the crypto scam loss question completely wrong. Using it well requires already knowing the difference, which is a useful thing to understand before the deadline arrives.
Topics: CRA changes 2026, unfiled tax returns, voluntary disclosure program, CRA chatbot, tax filing Canada
GUEST: David Rotfleisch |<a href="http://taxpage.com"> http://taxpage.com</a>
Originally aired on&nbsp;2026-03-10

Shane Hewitt & The Nightshift is your late-night companion for real talk, bold ideas, and unfiltered conversations that matter. Hosted by Canadian radio veteran Shane Hewitt, each episode dives into the headlines, human stories, and hidden truths shaping our world—always with curiosity, compassion, and a sharp edge.

From politics and pop culture to mental health, technology, and everyday life, this podcast is where night owls, deep thinkers, and curious minds come to connect. Featuring expert guests, passionate callers, and Shane’s signature style—thoughtful, fearless, and refreshingly real.

If you crave meaningful dialogue, smart perspectives, and late-night radio energy in podcast form, subscribe now and join The Nightshift.

Shane Hewitt &amp; The Nightshift is your late-night companion for real talk, bold ideas, and unfiltered conversations that matter. Hosted by Canadian radio veteran Shane Hewitt, each episode dives into the headlines, human stories, and hidden truths shaping our world&mdash;always with curiosity, compassion, and a sharp edge.
From politics and pop culture to mental health, technology, and everyday life, this podcast is where night owls, deep thinkers, and curious minds come to connect. Featuring expert guests, passionate callers, and Shane&rsquo;s signature style&mdash;thoughtful, fearless, and refreshingly real.
If you crave meaningful dialogue, smart perspectives, and late-night radio energy in podcast form, subscribe now and join The Nightshift.

Shane Hewitt and The Nightshift

Shane Hewitt is known for his engaging and relatable on-air personality, which captivates listeners. His ability to blend insightful commentary with humour and empathy creates a genuine connection with listeners.  Shane Hewitt and the Night Shift provides relatable content, informative discussions and expert insights – along with a balance of anecdotes and entertainment.

Shane Hewitt is known for his engaging and relatable on-air personality, which captivates listeners. His ability to blend insightful commentary with humour and empathy creates a genuine connection with listeners.  Shane Hewitt and the Night Shift provides relatable content, informative discussions and expert insights – along with a balance of anecdotes and entertainment.