Mac Messages app won't send text message when in a group message

When I'm in a group message with an iphone user and an android user it always sends as an iMessage, and the android user never gets the message. Even when it says "Text Message" in the text box it still sends as an imessage. This sometimes happens on my iPhone, but not every time. When I message the android user separately on my mac it sends as a text.  I've never been able to send a text in a group message on my mac though. I have to end up sending messages separately to the android user. The android user used to have an iPhone, but I've checked his phone number on this website https://selfsolve.apple.com/deregister-imessage and it says his phone number isn't registered to iMessage. He's also said he removed his phone number from his iPad. What could be causing this?

Hi,
If you add a Land Line number to your own Address Card in Contacts  (Card Menu > My Card) and then type your name in to the "To" spot in Messages on the Mac you will see the Land Line also listed as a potential iMessages contact number.
That is to say until it contacts any number the number involved will show a greyed out iMessages listing next to it.
For this Screen Grab I somewhat forced the issue to isolate my Land Line.
In the top bar it is listed as a potential iMessages contact.
As I have pressed enter it has gone a stage further and told me it is not Registered.
Whilst iMessages contacts that have worked are marked with a blue Speech Bubble for iMessages SMS/text ones have a green Indicator that says Text (as opposed to the AIM or Jabber  or Yahoo listed ones)
A less forced one
An iPhone is listed first.
The options are then the Land Line and then two email addresses both of which have been used before.
I too have noticed that trying to send an SMS text messages to a Number does not seem selectable on the Mac version (Click and hold and "Send as SMS" is not an option)
Hopefully this can be set up so the app can recognise Non iPhones in some way.
I have yet to find a way to start an SMS conversation from the Mac.
8:29 pm      Wednesday; December 24, 2014
​  iMac 2.5Ghz i5 2011 (Mavericks 10.9)
 G4/1GhzDual MDD (Leopard 10.5.8)
 MacBookPro 2Gb (Snow Leopard 10.6.8)
 Mac OS X (10.6.8),
 Couple of iPhones and an iPad

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