For some reason Telstra is blocking my Windows Live from sending emails to those I have replied to no matter who they are. I can answer emails form Telstra Webmail but if I try and do so for my Windows Live account it wont get sent and Telstra is telling me I am sending spam.
This has been happening for the last 3 days earlier this week the emails were going OK, and they were also being sent okay when I moved over to Telstra back in July. I do not know why and neither does Telstra customer Service, at one stage they blamed Microsoft last week when it was happening and the nit righted itself and started working and now it isn't.
I have used the Ports that Telstra tells me and as I said it was working but now it isn't' again. When I look in my Webmail account it says they are sent but they are not. somethign is wrong somewhere in Telstra webmail not my email.
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You're not alone in this, as I'm having exactly the same issues - read my story here.
The Telstra help desk kept saying it's an app (ie your software) problem, but I do have exactly the same issue with an iPhone too. You can see how hard I tried to solve it. Like you, this issue has only just happened from around the start of this week.
I did have one point of difference though in that webmail was working for me both incoming and outgoing (hence the help desk pointing the finger at Microsoft) although I haven't rechecked that to see if it has changed.
In the end I resorted to creating a GMail account just for sending out email (you can set up GMail to make it look as though your email is from your normal BigPond address)
However, this is a laborious workaround and not simple.
I'm with you on this one - I think the answer may well lie outside our own control - I was able to replicate the issue with a different pc and even different email software.
Here's hoping there's an answer soon.