Here are the steps:
Note: If you are new to Word Merges (you are using the "Built-in" letters), you'll need to set up a Template in word that has your letter and the fields. There are some sample templates on your computer at C:\Chabad Management System\Sample Templates. You don't have to generate all your letters via Word, but to use the email feature, you must output your letters to Word Merge, after that, you can filter to the larger amounts and generate those letters on paper as usual. Once word opens, click the Merge to Email button. See http://support.chabadms.com/KB/a308/.aspx for some more details on Merging to Emails where the same principle applies. Feature implemented in version 9.5.11 *Please check with your accountant/tax preparer/lawyer if email receipts in your area are sufficient and what amount threshold, if any, a paper receipt is required for tax deductible donations.
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