Since I've updated iOS 13 (Signal Version: 2.40.0.21) Attachments (Images, Videos, or Docs) failed to be sent.
Actual result: As soon as I hit the send button Signal tries to upload the image and eventually gives up and fails. It then blocks the next set of messages from being sent. After a minute or two once you the red box appears and you delete that message (or actually still don't know or understand) the queue of messages clears up and starts sending texts at least. Once I try to upload any media it loops through the whole thing again.
Expected result: You shouldn't have a dead queue of messages.

Device: iPhone XS
iOS version: iOS 13 beta 1
Signal version: 2.40.0.21
https://debuglogs.org/611436c5e4ebf2ead72cb3945825547e8f799a1ced2155d728126ba92d132540.zip
Re-posting for more visibility, as suggested by
, the current workaround or temp fix is mentioned
- Remember to clean up certificates once Signal has officially issued a fix for this.
Same issue...
Also having this issue.
@n4nd0br @jasonborchardt Please do not bump issues like that. From CONTRIBUTING.md:
Don’t bump issues
Every time someone comments on an issue, GitHub sends an email to hundreds of people. Bumping issues with a “+1” (or asking for updates) generates a lot of unnecessary email notifications and does not help anyone solve the issue any faster. Please be respectful of everyone’s time and only comment when you have new information to add.
If you just want to say that you have the same issue, you can add the :+1: reaction to the original issue post, which does not send useless notifications.
For me, even plaintext fails.
In addition to this, receiving images also seems broken for me in iOS 13 beta. The image fails to load (progress bar stays empty) and the retry arrow appears, repeat.
Same issues persist in iOS 13 beta2. Sending and receiving fail as well as uploading own profile image.
So this was cross posted in the Android tracker with details and a solution and I’ve been waiting for this to update. Here is the information from reddit cause and temporary solution.
Why does signal use a self-signed cert in the first place?
A self-signed cert is not bad in itself. It doesn't weaken the cryptography between client and server. But without signature from a publicly trusted CA, it leads to failure modes described in this issue.
Also technically, the cert isn't selfsigned. It appears that TextSecure (a.k.a Whisper Systems) are maintaining their own PKI, and the cert is signed by them.
This is resolved in the latest beta release of our app. If you're running the iOS 13 beta, we encourage you to install this update from TestFlight.
If you haven't used the beta version of Signal before you can join here: https://testflight.apple.com/join/8FHtd1Jq
Fixed for me at 2.40.2.0.
Thanks for fixing the issue, people who added a cert by themselves (according to , consider removing the added cert now that Signal shipped the solution in 2.40.2.0.
2.40.2.0 fixed sending and receiving images and voice messages and also setting a profile picture.
Running newest Beta version (2.43.0.7) and iOS 13.0 and still having issues sending/receiving images as well as setting a profile picture.
Trying to resend gives this error "SSL error has occurred and a secure connection to the server cannot be made."
@jmmiller60601 what version of iOS 13 are you running? This issue was fixed by Apple in 13.0 beta 6, it will not work on earlier versions.
Most helpful comment
In addition to this, receiving images also seems broken for me in iOS 13 beta. The image fails to load (progress bar stays empty) and the retry arrow appears, repeat.