Issues with iMessage when switching data carrier (wifi - cellular)

So I have had this issue with my 5S and now my 6+ in iMessage. Not *always* but often enough I've run into issues sending messages via iMessage when I associate with wifi in that they don't send. I'll get an error message saying "not delivered" and it will stack as many outgoing messages I try to send. However, if I force the first message to send as text, subsequent messages will go through afterwards without issue. If I go from wifi to cellular I have no issues whatsoever and when I have these issues on wifi, my data works fine (incoming emails, Facebook notifications, etc.). I used to run cellular data only because I had unlimited but now I have a cap so I intend on using wifi when possible...but to have to send my first message as a text just so I can use iMessage is annoying...

Hi there BigDogg795,
I would recommend taking a look at the troubleshooting steps for iMessage found in the article below. 
iOS: Troubleshooting Messages - Apple Support
To resolve issues with sending and receiving iMessages, follow these steps
Check iMessage system status for current service issues.
Go to Settings > Messages > Send & Receive and make sure that you registered iMessage with your phone number or Apple ID and that you selected iMessage for use. If the phone number or Apple ID isn't available for use, troubleshoot iMessage registration.
Open Safari and navigate to www.apple.com to verify data connectivity. If a data connection isn't available, troubleshoot cellular data or a Wi-Fi connection.
iMessage over cellular data might not be available while you're on a call. Only 3G and faster GSM networks support simultaneous data and voice calls. Learn which network your phone supports. If your network doesn't support simultaneous data and voice calls, go to Settings > Wi-Fi and turn Wi-Fi on to use iMessage while you're on a call.
Restart your device.
Tap Settings > General > Reset > Reset Network Settings on your iPhone.
If you still can't send or receive an iMessage, follow these steps
Make sure that the contact trying to message you isn't blocked in Settings > Messages > Blocked.
Make sure that the contact you're trying to send a message to is registered with iMessage.
If the issue occurs with a specific contact or contacts, back up or forward important messages and delete your current messaging threads with the contact. Create a new message to the contact and try again.
If the issue occurs with a specific contact or contacts, delete and recreate the contact in the Contacts app. Create a new message to the newly created contact and try again.
Back up and restore your device as new.
-Griff W.

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