If I have receipts for Goodwill donations totaling less than $5,000 , do I also need a letter from Goodwill?

It depends on the detail of the receipts you kept.

For noncash donations, you must get and keep a receipt or letter from the charitable organization showing:

• Organization's name and address
• Donation's date and location
• Donated property's description -- but not necessarily its value
• If the qualified organization gave you goods or services for contributing, a description and good faith estimate of the goods' and services' value
• If you received an intangible religious benefit, a statement that was the only benefit. It doesn't need to describe or estimate the value of the intangible religious benefit.

The charity must give you the acknowledgment on or before the earlier of:

• Date you filed your return for the year you make the contribution
• Due date, including extensions, for filing your return

You should also keep reliable written records with this information:

• Fair market value of the property when you donated it, and how you determined the fair market value. If it was determined by appraisal, keep a copy of the signed appraisal.
• Cost or other basis of the property if you must reduce its fair market value by appreciation. Your records should also include the amount of the reduction and how you figured it. If choosing the 50% limit instead of the 30% limit on certain capital-gain property, you must keep a record that shows:
  • Years you chose the 50% limit
  • Contributions for the current year when the choice applies
  • Carryovers from prior years when the choice applies
• Amount you claim as a deduction for the tax year as a result of the contribution. This applies if you contribute less than an entire interest in the property during the tax year. The records must include:
  • Amount claimed as a deduction in earlier years for contributions of other interests in this property
  • Name and address of each organization to which you contributed the other interests
  • Place where such tangible property is located or kept
  • Name of any person in possession of the property -- other than the organization you contributed to
• Terms of any conditions attached to the gift of property
• How you acquired the property, including:
  • Purchase
  • Gift
  • Bequest
  • Inheritance
  • Exchange
• Approximate date you acquired the property or substantially completed it if you did 1 of these:
  • Created the property
  • Produced the property
  • Manufactured the property
• Cost or other basis, and any adjustments to the basis, of property held less than 12 months and, if available, cost or other basis of property held 12 months or more. However, this requirement doesn't apply to publicly traded securities.

If you're unable to provide information on either the date you acquired the property or the cost basis of the property, you must attach an explanation to your return. This applies only if you have reasonable cause for not being able to provide the date and cost-basis information.