The default Messages app on iPhone shows messages’ timestamps on the beginning of an active conversation and then it stops displaying timestamps of the next message until it thinks that timestamps need to be displayed on the next conversation.
If you want to set the messages app to always show timestamps all the time, then you definitely should install SMS Timestamps cydia tweak.
This tweak changes the default habit of Messages app to set timestamps manually so that you can see timestamps on every single message or you can set it be displayed after a certain period of time (1 minute, 5 minutes, 10 minutes).
Inside SMS Timestamps settings, you can enable/disable regular timestamps. And if you enable SMS Timestamps, you will be able to see the detailed timestamps of your messages according to your time constraints setting.
In Time Constrains option, you can configure how the timestamps will be displayed on Messages app, it could be every message, after 1 minutes, 5 minutes, or 10 minutes (after the last time of timestamps displayed).
Name: SMS Timestamps
Author: Gabrio Barbieri
Price: FREE Cydia Tweaks
Useful and one of the best cydia tweaks for iOS Messaging.