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Southwest actually posted a travel advisory about this on their home page, here is the link:
https://www.southwest.com/html/advisories/swa_travel_advisory_20199101570725201165.html
Customer | Home airport DCA
Re: Updated SW app won't send boarding pass to Apple Wallet
Re: Updated SW app won't send boarding pass to Apple Wallet
10-25-2019 09:12 PM
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It is clearly an Apple IOS 13 issue. Passes from American Air will not load either. The IOS 13 update has been one of the buggiest and most irritating things I have ever seen. Maybe they will fix it, but there are dozens, if not hundreds of things that don't work with this update. Very disappointed.
@phxflyboy wrote:Did you update to the newest iOS a week or so ago? That could be the issue. I will say that as I'm writing this, I'm sitting at my gate at Midway Airport, just used the mobile boarding pass, and everything went just fine. The only odd thing I'm seeing now is that notifications don't seem to be going to my Apple watch, as they used to. That has been happening for a couple months now. New iOS 13 coming out in the next couple weeks, maybe that will fix everything, although I believe the issues are on SW's end.
Re: Updated SW app won't send boarding pass to Apple Wallet
Re: Updated SW app won't send boarding pass to Apple Wallet
10-25-2019 09:21 PM
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My IOS updates are automatic so the latest one is installed. This is definitely an Apple problem to fix. Amazing this is happening.
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Having the same issue. iPhone6 (shame!) iOS 12.4.1. Worked fine a few weeks ago.
Also - I have NEVER been able to get WN boarding passes on my lock screen. Yes, I have that option selected.
Re: Updated SW app won't send boarding pass to Apple Wallet
Re: Updated SW app won't send boarding pass to Apple Wallet
10-09-2019 08:57 PM
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Same issue here, it worked a week ago, and I do not see an update to iOS in the last week so it must be something on the backend.
Re: Updated SW app won't send boarding pass to Apple Wallet
Re: Updated SW app won't send boarding pass to Apple Wallet
10-10-2019 12:56 AM
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Same bug is back again. You’ve been pushing out the same bug repeatedly for more than 6 months.
Re: Updated SW app won't send boarding pass to Apple Wallet
Re: Updated SW app won't send boarding pass to Apple Wallet
10-10-2019 01:51 AM
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Seeing the same issue - started today. App was working and sent my orig flights boarding pass to wallet and went to check for my return flight and hit the weird blue pass and no wallet option.
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The same issue here, iPhone 7, newest iOS version. Cannot add mobile passes to Apple Wallet. Disappointing 😞
Re: Updated SW app won't send boarding pass to Apple Wallet
Re: Updated SW app won't send boarding pass to Apple Wallet
10-10-2019 10:20 AM
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Folks,
This has reappeared today. I am on iPhone / iOS 13.1.2.. And checking app updates, SWA mobile app is up to date. The Add to Apple Wallet has disappeared.
Re: Updated SW app won't send boarding pass to Apple Wallet
Re: Updated SW app won't send boarding pass to Apple Wallet
01-10-2020 12:43 PM
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Having the same issue now. Has worked in the past. No option to 'export' to Apple Wallet.