When using CSUPLOAD to upload your VHD to use with VM role, it is possible you may receive the following error:
Using the saved connection string...
Using temporary directory C:\AzureVM \Virtual Hard Disks...
An unexpected error occurred: The request channel timed out attempting to send after 00:01:00. Increase the timeout value passed to the call to Request or increase the SendTimeout value on the Binding. The time allotted to this operation may have been a portion of a longer timeout.
This error will occurred if connection to Windows Azure Management site could not be established due to general connectivity issues. The CSUPLOAD tool is using credentials set in the connection string and if the connection could not be established then you will get this error.
To confirm it you can run the following command
> CSUPLOAD get-location
And if there is any kind of connectivity problem from your machine to Windows Azure Management Portal, you will get the exact same error which you have received during VHD upload.
To solve this problem you will need to check your network settings and networking components, i.e. proxy, firewall etc. If you try to run the same command outside the network boundary or some other please it could verify that the issue is with your network where CSUPLOAD is running.