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answers:

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Using iTextSharp (and c#/ASP.NET) is it possible to open an RTF document, manipulate it by replacing some text, insert an image (WMF or PNG), and the export that manipulated document to a PDF document that retains the formatting of the original RTF document?

Essentially I'm hoping to create a simple mail merge solution with the template being in RTF and the output needing to be in PDF. This needs to run on an ASP.NET server.

A: 

No it is not possible per se with iTextSharp. Better approach will be to use Word Object to open document, do mailmerge and then save those documents ad HTML. Now you can use iTextSharp to parse html and create PDF.

TheVillageIdiot