Cannot send/reply email on Mac and iPhone

SOMETIMES I cannot send or reply emails on my Mac, not all the time though. Went to Apple Store where a Genius helped me reset my mail app but turning it off and back on again, it worked there and then but when I got home, I'm still getting the below same message when I try to send or reply sometimes:
"Connections to the server "p08-smtp.mail.me.com" on the default ports times out.
Select a different outgoing mail server from the list below or click Try Layer to leave the message in your Outbox until if can be sent."
This happens on my iPhone as well. Sometimes when I reply to someone's email it'd just sit in the Outbox for more then a day despite numerous attempts to resend. In the end I could only delete it from Outbox and send a new one again. I tried to find answers online without luck, can someone please help?
Note that if I send/reply on iCloud website, everything works perfectly!
Many thanks!

Hi Chi Chi Cheng,
Welcome to Apple Support Communities.
We have a few articles than can help troubleshoot issues sending mail on both Mac and iOS.
You may find these links helpful:
OS X Mail: Troubleshooting sending and receiving email messages
http://support.apple.com/kb/ts3276
iOS: Unable to send or receive email
http://support.apple.com/kb/ts3899
iCloud: Troubleshooting iCloud Mail
http://support.apple.com/kb/ts4002
Best,
Jeremy

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