Can I Deduct My Medical and Dental Expenses? Determine if your medical and dental expenses are deductible. Can I Deduct My Mortgage-Related Expenses? Determine if you can deduct mortgage interest, mortgage insurance premiums and other mortgage-related expenses. Can I Deduct My Charitable Contributions? Determine if your charitable contributions are deductible. Can I Claim My Expenses as Miscellaneous Itemized Deductions on Schedule A? Determine if you can deduct certain expenses related to producing or collecting taxable income. Can I Deduct Personal Taxes That I Pay as an Itemized Deduction on Schedule A? Determine if personal taxes you paid are deductible as an itemized deduction on Schedule A. Are My Work-Related Education Expenses Deductible? Determine whether expenses you paid for work-related education are deductible and how to report them.