I'd start by reviewing the application – looking to understand what areas of the application may be vulnerable to being used and displayed on a mobile browser.
In terms of display issues, look for HTML heavy pages, such as pages with style sheets designed for larger display areas. Also look for ages with Flash, bulleted lists, buttons and links. A review of some pages with these elements will likely quickly reveal what's problematic versus what still looks and functions well. Also worth checking is the sitemap since it's often a list designed to be displayed both wide and tend to be long. In some cases, the sitemap may have to be redesigned to display well with a mobile device.
I mentioned in an article published on SearchSoftwareQuality.com this past summer, Mobile testing: Three vulnerable areas to test , to look for SSL pages and check that switching in and out of secure mode still works. Navigation, browsing and cookie crumb trails are areas to check the functionality hasn't been impacted.
I realize this sounds like a great deal of effort and time, so consider starting with the lowest end device your company plans to support – start by looking for the worst case scenario and see what you find. Starting out in mobile testing is an exploration.
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