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Your iPhone is sending as imessage. When you get the undelivered message, click on the little red circle and choose to seND as text. You may have to repeat a couple of times before it remembers.
Apple does this to keep people on iphones, and to an extent it works. There are lawsuits on going in several states to get this changed.
The only, and I mean only solution to this is to use Google Hangouts as the Android users primary SMS client for a period of 45 days, yes 45 days exactly.
Then after 45 days they can use whatever app they want for SMS.
Just had this same exact issue last week... Wife has an iPhone 5.. we kept her old iPhone 4 as a backup.. I blew out the LCD in my Galaxy S4.. switched to her old iPhone while I waited
for the parts to come in to fix my Galaxy... Once the new LCD came in, I fixed the S4, everything working beautiful again..switched the service back.. Got texts from everybody but the wife... after giving her
some crap for ignoring me, she informed me that she was answering all my texts..
Turned out the two iPhones were set to imessage each other... had to turn it off on the old phone and on hers.. boom.. texts started coming thru again...
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