[tdemayParticipant]

Thanks for your immediate response. I built the extension method below from your example in WmlToHtmlConverter.cs. Posting it here for anyone that might need it.

Let me know if you have any thoughts on this. I doubled the font size because for some reason I don’t understand the FontSize that is used in the <w:sz> elements for the TextBox is doubled in the XML than what the user sees in the FontSize drop down in the UI.

        public static D.Size GetTextSize(this CWatermarkItemBase watermark, string runText)
        {
            D.FontStyle fs = D.FontStyle.Regular;
            if (watermark.FontBold) fs |= D.FontStyle.Bold;
            if (watermark.FontItalic) fs |= D.FontStyle.Italic;
            var sz = watermark.FontSize * 2;
            var proposedSize = new D.Size(int.MaxValue, int.MaxValue);
            D.Size sf;

            using (var ff = new D.FontFamily(watermark.FontFamily))
            {
                try
                {
                    using (var f = new D.Font(ff, (float)sz, fs))
                    {
                        const TextFormatFlags tff = TextFormatFlags.NoPadding;
                        sf = TextRenderer.MeasureText(runText, f, proposedSize, tff);
                    }
                }
                catch (ArgumentException)
                {
                    try
                    {
                        const D.FontStyle fs2 = D.FontStyle.Regular;
                        using (D.Font f = new D.Font(ff, (float)sz, fs2))
                        {
                            const TextFormatFlags tff = TextFormatFlags.NoPadding;
                            sf = TextRenderer.MeasureText(runText, f, proposedSize, tff);
                        }
                    }
                    catch (ArgumentException)
                    {
                        const D.FontStyle fs2 = D.FontStyle.Bold;
                        try
                        {
                            using (var f = new D.Font(ff, (float)sz, fs2))
                            {
                                const TextFormatFlags tff = TextFormatFlags.NoPadding;
                                sf = TextRenderer.MeasureText(runText, f, proposedSize, tff);
                            }
                        }
                        catch (ArgumentException)
                        {
                            // if both regular and bold fail, then get metrics for Times New Roman
                            // use the original FontStyle (in fs)
                            using (var ff2 = new D.FontFamily("Times New Roman"))
                            using (var f = new D.Font(ff2, (float)sz, fs))
                            {
                                const TextFormatFlags tff = TextFormatFlags.NoPadding;
                                sf = TextRenderer.MeasureText(runText, f, proposedSize, tff);
                            }
                        }
                    }
                }
            }
            const int multiplier = 5000;
            return new D.Size(sf.Width * multiplier, sf.Height * multiplier);
        }

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