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Issue resolved, if anyone is interested. The WebGateway itself was causing the Client to time out. I can't quite understand why, but once we created a specific Internet Zone allowing the following sites, the connection stopped timing out: *.edgesuite.net
*.live.com
*.lync.com
*.microsoft.com
*.microsoftonline-p.com
*.microsoftonline-p.net
*.microsoftonline.com
*.microsoftonline.net
*.office365.com
*.outlook.com
*.sharepoint.com
activation.sls.microsoft.com
microsoftonline-p.com
microsoftonline-p.net
microsoftonline.com
microsoftonline.net
odc.officeapps.live.com
office15client.microsoft.com
office365.com
ols.officeapps.live.com