Thanks for the clarification, kaskewes. As an iPhone user and mother of one teenager, I completely understand where you're coming from. I would like to provide further clarification regarding your messaging details via My Verizon. Message history will show in the order it was received via SMS only, so it will all depend on how the message was sent from his phone. For example, if one message was sent as SMS (green bubble) and the other message went through as iMessage (blue bubble), then the messaging history from your My Verizon may seem odd. The only way to test this out is by disabling iMessage from your son's phone and have him only use SMS (green bubble) so that you can monitor his messaging history online without any issues. To disable iMessage from his iPhone, please go to Settings>Messages>iMessage>off. Please let us know if you are able to view his messaging history online after using SMS only.
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I have the same exact problem with just one of our lines. No message logs showing up even though there are 1166 messages so far this month. I contacted Verizon and they said there is a problem with a server and opened a ticket with their tech support department. I first called about the problem on Thursday. It is now Sunday and as of yesterday someone told me it should be fixed by Tuesday.