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OF doesn't support manual sorting in context mode. Sorting in Context mode is controlled by the View Bar settings for grouping and sorting. If there is a tie between two items based on those criteria (or if grouping or sorting is turned off), then the order of the items in Planning mode is used. This lets people use the order of projects and actions in Planning mode as a fine-grained priority mechanism. (This has been debated on the forums. It's hard to see how manual rearranging in Context mode would work with the current scheme.)

One workaround for your purposes might be to abuse the duration column. You could turn on the estimated duration column (View → Columns → Estimate) and sort by duration. Then you could enter ascending numbers for your agenda items (1, 2, 3, …). Of course, this only works if you aren't already using estimated duration on these tasks for its stated purpose.
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Cheers,

Curt