Why are two servers viewing the same drive unable to view the same files?

I have two windows 2008R2 servers. Both are pointing to the same iSCSI drive on our SAN, but both servers don't see the same data.

Server 1 can write data to the SAN, and can immediately see what it wrote. Server 2, can NOT see what server 1 wrote after the last time server 2 was rebooted.

The OS doesn't seem to be an issue here. I have Win2K3 servers, Win2008 servers, and 2008R2 systems, all with the same problems.

Only the one that writes can read that data until the other one is rebooted.

Where can I start looking to try and resolve this problem?

I thought the whole point of clustering ( not what I am doing, but still ), was to have two systems point to the same SAN drive, and share common data. That leads me to believe that I should be able to read and write between the two systems sharing the same drive.

What am I missing here?

iSCSI presents block based storage to the Servers. In most scenarios the servers mount this storage with a filesystem (such as NTFS) that is owned and managed by one server only. NTFS (which is what you are probably using here) is not normally a cluster aware file system so if secondary hosts have visibility to the same volume they will either be locked out (hopefully) or will corrupt the volume.

For two separate machines to share an iSCSI volume concurrently you need to have a cluster aware file system that supports this. VMware's VMFS does this as does the Cluster Shared Volumes (CSV) clustered file system available in W2K8 R2 Hyper-V.

The simplest solution for you is to present the storage to one server and share that volume so that the second server can map to it using SMB.

Edited to add:
There's no real way around the double network hop if you opt for sharing out the volume via Windows but for most server applications you should be able to specify a UNC Path (\\Server\sharename) rather than a mapped drive letter. This will work if the service is running under an account that has rights to the share.

You don't say what sort of iSCSI target you have - it may be possible to configure it to act as (say) an SMB or NFS share directly. Windows Server 2008 R2 supports the Unix Interoperability components which includes an NFS client. This may provide you with a mechanism that avoids the double network hop but I can't comment on the performance, it might not be any better than the SMB share.