There are some cases where you may load a timeline using Twitter Kit on iOS 9 and all the tweets will show up but the images are missing. For example:
This occurs because some percentage of image traffic is directed to a CDN that is only signing responses with SHA1 certificates. To work around this issue, you may wish to add an ATS exception for pbs.twimg.com to your apps Info.plist (http://ste.vn/2015/06/10/configuring-app-transport-security-ios-9-osx-10-11/).
To investigate further you may wish to use nscurl:
nscurl --ats-diagnostics https://pbs.twimg.com/profile_images/2044921128/finals.png