Everytime I try sending a email to multiple emails, it have a server problem

Everytime I try sending a email to multiple emails, it have a server problem, it says "Cannot Send message using server hotmail" this only happen when sending to multiple emails, it work fine with one email address.

After multiple attempts i received a email from Hotmail Member Services <member_services@live.com>

Subject: Please Sign In.

Hello ................,

To continue sending messages, please sign in (http://mail.live.com) and validate your account.

This helps us stop automated programs from sending junk email.

Thank you for your help and patience!


Is this a mail Application issue sending multiple emails? or hotmail blocking me from sending emails? how to do i validate my computer to send an email to multiple emails



User uploaded file

MacBook Pro, OS X Mountain Lion (10.8.2)

Posted on Jul 22, 2013 7:32 AM

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17 replies

Jul 22, 2013 7:58 AM in response to BobTheFisherman

I don't know about all email systems but iCloud has the following limits.


  • The total number of messages you can send each day (200 messages)
  • The number of recipients to whom you can send each day (1000 recipients)
  • The maximum number of recipients per message (100 recipients)
  • The size of incoming and outgoing messages (20 MB)


So 32 addresses in one message would be less than a third of the addresses allowed.

Jul 22, 2013 8:25 AM in response to Csound1

The Email is Used for business dont need to use Icloud i have an Icloud email account already,


I also try this option in side outlook orginal mail site settings, the permission TAB.

at The bottom it has "Manage apps and services that can access your info"

User uploaded fileUser uploaded file After seeing this I am wondering if this is why its not allowing it, because no apps is showing their

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Everytime I try sending a email to multiple emails, it have a server problem

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