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How to Watch ‘Insecure’ Season 5 Premiere Online for Free on Apple TV, Roku, Fire TV, and Mobile

Lauren Forristal

Returning for the fifth and final season, the Emmy-winning HBO comedy series Insecure will reveal how the characters figure out who and what comes with them as they transfer into the next phase of their lives. The season premiere airs on October 24 at 10:00 ET. You can watch it with a 7-Day Free Trial of HBO Max via Hulu.

How to Watch ‘Insecure’ Season 5 Premiere

1. Get a Free Trial of HBO Max Through Hulu

If you are a new or current Hulu subscriber that has never tried HBO Max through Hulu, you’re in luck. Hulu is offering a 7-Day Free Trial to HBO Max through their streaming service.

New Hulu Subscribers

  • Click here to activate the offer
  • Click “Sign-Up Now”
  • Create Your Account
  • Click “Manage Add-Ons”
  • Add Your 7-Day Free Trial of HBO Max
  • Once you’re subscribed, use your Hulu credentials to log-in to the HBO Max App on your streaming device

Existing Hulu Subscribers

If you are an existing Hulu subscriber:

  • Click your Profile
  • Click “Account”
  • Click “Manage Add-Ons”
  • Add HBO Max Free Trial

2. Sign-up For HBO Max Directly

While it’s not a free trial, you could always sign-up for HBO Max for a month and stream “Dune” and then “King Richard” later this year.

How to Get HBO Max

  • Click here to sign-up
  • Click “Sign Up Now”
  • Select “Prepay & Save”
  • Create Your Account
  • Add Your Payment Information
  • Click “Start Subscription”

About ‘Insecure’

The comedy-drama television series, Insecure is mainly about the awkward, “insecure” moments and experiences of an African American woman. From the point of view of best friends, Issa (Issa Rae) and Molly (Yvonne Orji), both navigate living in their 20s, leaving their college days behind them, and dealing with new careers and relationships. Throughout the show, the women deal with internal struggles, the African American community, and their friendship.

Season 5 covers the characters as they evaluate their new and old relationships. The season will star series regulars Yvonne Orji, Jay Ellis, Natasha Rothwell, Amanda Seales, and Courtney Taylor. As audience members have watched them evolve throughout each season, it will be interesting to see where these ladies will end up when the show comes to an end.

In a New York Times interview, Issa Rae reflects on her conversation with head writer and co-executive producer Amy Aniobi in regards to ending the show. “I’ve got to credit Amy. We were really trying to find the right way to end the show, and she told us, ‘We keep trying to land the plane.’ Instead, she reminded us that the plane ride continues, and these characters are going to live on. That was so freeing to be able to say to each other, ‘Oh, we’re not ending this show.’ These characters that I know and I’ve grown with are going to continue to make decisions and live on.”

Insecure was created by Issa Rae & Larry Wilmore. It’s executive produced by Issa Rae, Prentice Penny, Melina Matsoukas, Michael Rotenberg, Dave Becky, Jonathan Berry, Amy Aniobi, and Jim Kleverweis.

The season 5 episodes of Insecure will be available to stream on HBO Max the day after airing on HBO.


October 9, 2016

Follows the awkward experiences and racy tribulations of a modern-day African-American woman.

How to Stream Inecure Season 5 Premiere for Free on Roku, Fire TV, Apple TV, iOS, and Android

There are six major streaming providers that offer Live TV Streaming. Four of these providers allow you to watch the Insecure season 5 premiere live on HBO using iOS, Android, Roku, Apple TV, Fire TV, Chromecast, and Web. They are DIRECTV STREAM, Hulu Live TV, and YouTube TV.

DTV STREAMfuboTVHuluPhiloSling TVYouTube
Sign UpFree TrialSign UpFree TrialFree TrialSign Up

All Live TV Streaming Options


Price: $139.99
Includes: HBO + 35 Top Cable Channels

Hulu Live TV

Price: $69.99

Add-on: $15 HBO
Includes: HBO

YouTube TV

Price: $64.99

Add-on: $15 HBO Max
Includes: HBO

AT&T TV Cash Back

Let us know your e-mail address to send your $75 Amazon Gift Card when you sign up for AT&T TV.

You will receive it ~2 weeks after you complete your first month of service.

Sling TV Cash Back

Let us know your e-mail address to send your $10 Amazon Gift Card when you sign up for Sling TV.

You will receive it ~2 weeks after you complete your first month of service.