Frequently Asked Questions

Welcome to the Open Enrollment FAQ for the 2027 Plan Year! Please see below for answers to common questions about:

If your question is not answered by the FAQ, please reach out to the Benefits Team at benefits@cityofmadison.com or (608) 266-4615.


General Questions, Dates, and Rates

This section of the FAQ addresses questions related to Open Enrollment more generally, including opportunities for in-person assistance, Open Enrollment dates, and general information about premium rates for the 2027 Plan Year. (Specific information about health insurance premium rates is in the Health Insurance section of the FAQ.)

What is Open Enrollment?

Open Enrollment (OE) is a period of time occurring once per year when eligible employees can enroll in, make changes to, or cancel their benefit options for health insurance, dental insurance, and/or vision insurance without a qualifying event, and enroll in Flexible Spending without a qualifying event.

When is Open Enrollment? When does it end?

In 2026, Open Enrollment for Health, Dental, and Vision Insurance runs from Monday, October 5 through Friday, October 30 at 4:30pm.

Open Enrollment for Flex Spending (and the Parking Account Benefit) will run from Monday, November 9 through Friday, November 20 at 4:30pm.

All enrollment(s), change(s), and cancellation(s) submitted during Open Enrollment take effect January 1, 2027.

When do Open Enrollment changes take effect?

All enrollment(s), change(s), and cancellation(s) submitted during Open Enrollment take effect January 1, 2027.

Is documentation required for Open Enrollment changes?

No documentation is required for dental or vision insurance. However, ETF now requires documentation (proof of marriage, parenthood, and/or legal guardianship) for all spouses and/or dependent(s) who are being newly added to health insurance, including Open Enrollment changes.

If you are newly adding a spouse, (step)child, and/or legal ward to your health insurance for the 2027 Plan Year, you must provide documentation in the My Insurance Benefits portal. Until documentation has been provided, your Open Enrollment change will not be approved.

Can I receive in-person help with Open Enrollment?

Yes! There are several options for you:

  • General assistance: HR front desk staff are trained to answer basic questions about Open Enrollment, including assisting with making changes to health insurance via the My Insurance Benefits portal or to dental/vision insurance via the Employee Self Service (ESS) portal. The HR front desk will be open 8:00am-4:30pm Monday-Friday.
  • Regular benefits assistance: The Benefits Team will have a representative available from 2:30-4:30pm on Tuesdays and from 8:30-10:30am on Thursdays to assist with Open Enrollment questions in-person at the City of Madison Human Resources office (215 Martin Luther King Jr. Blvd. Ste. 261).
  • ETF forums: ETF will be hosting a number of insurance benefits forums during Open Enrollment for you to learn about the 2027 Plan Year. These webinars are similar to a virtual Vendor Fair and provide the opportunity to ask questions directly to health plans and vendors like Navitus (pharmacy benefit) and WebMD (Well Wisconsin). Preregistration is required - visit etf.wi.gov/insurance to register.
  • NEW! On-site benefits assistance: This year, representative(s) from the Benefits Team and/or Administrative Support Team will be on-site at various City locations to provide dedicated in-person assistance with Open Enrollment questions, health insurance changes via the My Insurance Benefits portal, and dental/vision changes via the Employee Self Service (ESS) portal. These in-person help sessions are in lieu of an in-person Vendor Fair. Sessions are scheduled at the following dates and times:
LocationDateTime(s)
1120 Sayle St. (Traffic Engineering, Parking)10/12/20262:00pm-4:00pm
1501 W Badger Rd. (Streets West)10/14/20267:00am-8:00am, 2:00pm-3:00pm
1600 Emil St. (Engineering)10/14/20262:00pm-4:00pm
110 S Paterson St. (Water Utility)10/15/20267:00am-8:00am, 2:00pm-3:00pm
4602 Sycamore Ave. (Streets East)10/21/20267:00am-8:00am, 2:00pm-3:00pm
Madison Municipal Building (MMB) Room 20410/21/20269:00am-12:00pm
4151 Nakoosa Trail (Fleet)10/21/202612:00pm-1:00pm
1 S Ingersoll St, Monona Conf. Room (Metro)10/22/202610:00am-1:00pm
1402 Wingra Creek Pkwy (Parks - Goodman)10/23/20261:00pm-3:00pm

Is there an in-person Vendor Fair this year?

No. However, while there is not an in-person Vendor Fair this year, ETF will be hosting a number of insurance benefits forums during Open Enrollment for you to learn about the 2027 Plan Year. These webinars are similar to a virtual Vendor Fair and provide the opportunity to ask questions directly to health plans and vendors like Navitus (pharmacy benefit) and WebMD (Well Wisconsin). Preregistration is required - visit etf.wi.gov/insurance to register.

Additionally, representative(s) from the Benefits Team and/or Administrative Support Team will be on-site at various City locations to provide dedicated in-person assistance with Open Enrollment questions, health insurance changes via the My Insurance Benefits portal, and dental/vision changes via the Employee Self Service (ESS) portal. Sessions are scheduled at the following dates and times:

LocationDateTime(s)
1120 Sayle St. (Traffic Engineering, Parking)10/12/20262:00pm-4:00pm
1501 W Badger Rd. (Streets West)10/14/20267:00am-8:00am, 2:00pm-3:00pm
1600 Emil St. (Engineering)10/14/20262:00pm-4:00pm
110 S Paterson St. (Water Utility)10/15/20267:00am-8:00am, 2:00pm-3:00pm
4602 Sycamore Ave. (Streets East)10/21/20267:00am-8:00am, 2:00pm-3:00pm
Madison Municipal Building (MMB) Room 20410/21/20269:00am-12:00pm
4151 Nakoosa Trail (Fleet)10/21/202612:00pm-1:00pm
1 S Ingersoll St, Monona Conf. Room (Metro)10/22/202610:00am-1:00pm
1402 Wingra Creek Pkwy (Parks - Goodman)10/23/20261:00pm-3:00pm

Where are the Open Enrollment memos?

Open Enrollment informational packets for the 2027 Plan Year are available electronically. An email directing you to log on to the Employee Self Service (ESS) portal to review a Notification with more information about Open Enrollment was sent to the email address on file for you in MUNIS on the first day of Open Enrollment. If you have not already done so, please log on to ESS and review the Notification as soon as possible. The Notification will confirm your Benefit Group for the memo packet (A, B, C, D, or E) and will also provide a link to the HR Open Enrollment website, where you can review packets, ratesheets, and other Open Enrollment documents for the 2027 Plan Year.

Hardcopy Open Enrollment packets are available upon request to benefits@cityofmadison.com.  

IMPORTANT: If you are eligible for benefit(s), please make sure you review the memo packets and rates even if you are not planning to make any changes for 2027! This ensures you are making an informed decision about the 2027 Plan Year.

What should I do if I need an accommodation?

If you need a reasonable accommodation with regard to a disability or medical condition, please reach out to Leah Reinardy at (608) 267-1156 or accommodations@cityofmadison.com. 

I don't want to make changes to my health, dental, and/or vision insurance. Do I have to do anything during Open Enrollment?

If you do not want to make changes to health, dental, and/or vision insurance, no action is required. If you do not submit changes, any existing enrollment(s) will automatically continue into 2027 at 2027 rates.

However, even if you are not making changes, be sure to read the memo packet for your Benefit Group (and if eligible for health insurance, review the health + pharmacy information in the 2027 Decision Guide) to stay informed about what’s changing in 2027.

What are the rates for my health, dental, and/or vision insurance in 2026?

Please refer to the Open Enrollment memo packets and website for more information about rates, including expanded premium ratesheets for health insurance. In 2027, all Open Enrollment materials are available digitally on the Open Enrollment website.

Please note that in 2027, rates are changing for both health and dental insurance.

Health Insurance

This section of the FAQ answers common questions about health insurance, including how to make changes, clarifications for the health form, and context for 2027 Plan Year premium rates. Please ignore the premiums that appear in My Insurance Benefits - those amounts do not include the employer contribution to the premium.

Additionally, if you are newly adding a spouse, (step)child, and/or legal ward to your health insurance for the 2027 Plan Year, make sure you have proof of marriage/parenthood/guardianship documentation ready to upload to the portal! ETF now requires documentation for all newly added spouse/dependent(s), including Open Enrollment changes.

How do I make an Open Enrollment change to my health insurance?

This year, the only way to make an Open Enrollment change to health insurance is via the My Insurance Benefits portal online.

Recommendations:

  • Log in to My Insurance Benefits as soon as possible to make sure you can access the portal. Do not wait until the last minute! This is primarily because you need a MyWisconsin ID to access My Insurance Benefits. MyWisconsin ID is separate from all City login credentials, and can take 1-2 days to finish processing after you set up an account - which means that, if you wait until the last minute, you may miss the deadline while your MyWisconsin ID finishes configuring.
  • Review the My Insurance Benefits FAQ for answers to common questions about the My Insurance Benefits portal.
  • Ignore the premium rates listed in the portal - they do not include the employer premium contribution. Review the ratesheets on the Open Enrollment website for accurate 2027 rates for City employees.
  • Review the Changing Health Coverage page for instructions on how to submit change(s) to health insurance via My Insurance Benefits.
  • If you are newly adding a spouse, (step)child, and/or legal ward to your health insurance for the 2027 Plan Year, make sure you have proof of marriage/parenthood/guardianship documentation ready to upload to the portal. ETF now requires documentation for all newly added spouse/dependent(s), including Open Enrollment changes.
  • If you need to request a paper form as a reasonable accommodation for a disability, please reach out to Occupational Accommodations Specialist Leah Reinardy at (608) 267-1156 or lreinardy@cityofmadison.com. 

What changes can I make to my health insurance?

Employees may want to change health plans, go from Individual to Family coverage, go from Family to Individual coverage, add dependent(s), remove dependent(s), enroll in coverage, or cancel coverage.

IMPORTANT: new this year, ETF is requiring documentation (proof of marriage, parenthood, and/or legal guardianship) for all newly added spouses and/or dependent(s), including Open Enrollment changes.

If you are newly adding a spouse, (step)child, and/or legal ward to your health insurance for the 2027 Plan Year, you must provide documentation in the portal. Until documentation has been provided, your Open Enrollment change will not be approved.

Additionally, Open Enrollment changes are still subject to ETF regulations and restrictions. For example:

  • You cannot remove court-ordered dependent(s) as an Open Enrollment change.
  • If you are enrolled in Family coverage for health insurance, you must cover any/all spouse + minor dependent(s) on your Family plan.
  • ETF does not allow dual coverage within the Group Health Insurance Program (but does allow dual coverage between a GHIP plan and a non-GHIP employer or insurance provider's plan).

If you have questions about whether a specific change is possible, please reach out to the HR Benefits Team directly at (608) 266-4615 or benefits@cityofmadison.com. 

I need to make a qualifying event change and an Open Enrollment change for health insurance. What should I do?

If you need to make a qualifying event change (e.g. marriage, birth/adoption, divorce, new hire enrollment, etc.) and also want to submit an Open Enrollment change, you will need to submit your qualifying event change first. Additionally, your qualifying event change must be fully approved in the portal - with all documentation provided - before you can submit your Open Enrollment change.

For these reasons, if this applies to you please contact the Benefits Team at benefits@cityofmadison.com as soon as possible - before submitting anything via My Insurance Benefits.

The premiums in My Insurance Benefits are different from the premiums on the ratesheet - why?

The health insurance premiums displayed in My Insurance Benefits are the full premium amount, without the employer contribution. For this reason, please ignore the premiums in My Insurance Benefits. To confirm accurate premiums (with employer contributions) for 2027, please refer to the ratesheet included in the memo packet for your Benefit Group and on the Open Enrollment page.

The My Insurance Benefits FAQ also has detailed information about how premiums display in My Insurance Benefits.

Is there an Opt-Out Incentive for City employees to waive or cancel City health insurance?

Unfortunately, no. The Opt-Out Incentive is only an option for certain State employees, and does not apply to City employees. There is no compensation or incentive to waive or cancel City benefits.

My premium went up significantly. Why did this happen?

The 88% of average maximum employer contribution calculation for the City of Madison can only take into account qualified Tier 1 network providers who have service in Dane County. 2027 is the fourth year in a row that Dean’s rates are high enough they do not qualify for Tier 1, and will be the first year that Quartz UW Health's rates do not qualify them for Tier 1, either. Unfortunately, this means that the 88% of average calculations ETF made for the City for 2027 only take into account Group Health Cooperative of South Central Wisconsin - Dane Choice, which lessens the impact of the employer contribution.

More information about 2027 medical premium increases is available on the ETF website. ETF provides details about this year’s rate increases, their plans to help manage future rate increases, and contact information for the Group Insurance Board for members to share concerns about premium rate increases directly with the Board.

Is there a way for me to share my concerns about premium increases with ETF?

Yes. Members of the Group Health Insurance Program can share their concerns about health insurance premium increases by contacting the Group Insurance Board. There are two ways to share feedback/concerns:

Email:   BoardFeedback@etf.wi.gov

Mail:  Department of Employee Trust Funds
             Board Liaison
             PO Box 7931
             Madison, WI 53707-7931

Dental and Vision Insurance

This section of the FAQ answers common questions about dental and vision insurance, including how to make changes and ESS troubleshooting.

Can I make dental or vision changes for Open Enrollment via paper or PDF forms?

No. The only way to make Open Enrollment changes to dental or vision insurance is via the Employee Self Service (ESS) portal online. Any paper or PDF forms HR receives will be rejected.

Instructions on how to submit changes via ESS are available in the ESS Resource Menu in the upper-right corner of your computer screen.

I don't remember my ESS username or password. How do I log on?

Your ESS username is your MUNIS/City ID number and can be found on your paystub in the upper left-hand corner. HR or your Payroll Clerk can also confirm your ESS username for you. If you do not remember your password and/or are locked out of your account, please call IT at (608) 266-4193 to reset your password.

We strongly recommend you try to log on to ESS early in the Open Enrollment period to make sure you are able to access the portal.

IMPORTANT: ESS login now requires employees to answer two security questions (in addition to entering your password) for added security. It takes more time to reset your security questions than it does to reset your password. Because of this, we strongly recommend you do not leave your dental/vision changes to the last minute, as if you need to reset your security questions, you may not receive a response in time to log in to ESS and submit your changes.

I'm in ESS, but I'm not sure how to submit my changes. Can you help?

Once you are logged in to ESS, you can navigate to the Resource Menu (an icon that looks like a piece of paper with the corner folded over; on a computer, this will be in the upper-right corner). The 2027 Dental/Vision ESS instructions are one of the first resources available. If you open these in a new tab, you can reference them while you make your changes in the Benefits --> Open Enrollment section of ESS.

How should I make sure my spouse is covered on my dental and/or vision insurance?

If you are married and wish to cover your spouse on your dental and/or vision insurance: 

  1. Make sure you have selected a coverage level that includes your spouse (Employee + Spouse or Entire Family).
  2. Make sure your spouse’s information is listed in ESS. If your spouse is not listed as a person to be covered, you must add your spouse’s information as a “dependent” in ESS.
  3. Once all family member(s) who should be covered on your plan(s) are listed, be sure to submit your election(s).

ESS is asking for my dependents' Social Security Numbers (SSNs). Do I have to provide those?

No. You can put in your own SSN or a placeholder SSN like 123-45-6789. If ESS will not let you save a given number, please try a different one.

I'm not making changes to dental and/or vision insurance - do I need to submit anything?

No. If you are not making changes to either dental or vision insurance, please do not submit anything via ESS. If no changes are submitted, any existing enrollment(s) will automatically continue into 2027 at 2027 rates.

With that said, if you are changing your election for dental but not vision (or vice versa), you will need to select "no changes" for the benefit you are not changing in order to submit the changes to the benefit you are changing.

Flex Spending

This section of the FAQ answers common questions about Flex Spending, including how it works, the difference between Healthcare FSA and DCAP, and how to enroll for the 2027 Plan Year.

When is Flex Spending Open Enrollment?

In 2026, Open Enrollment for 2027 Plan Year Flex Spending runs from Monday, November 9 through Friday, November 20 at 4:30pm.

What is Flex Spending?

The City’s Flexible Spending Account (commonly referred to as “Flex Spending,” “Flex,” or “FSA”) program allows employees to designate pre-tax dollars for eligible expenses. There are two types of FSAs:

  • Healthcare FSA: funds elected for Healthcare FSA (also called Medical FSA) can be used for eligible medical expenses incurred by you, your spouse, and/or your qualified dependent(s) (as defined by IRS regulations) during the Plan Year and grace period.
  • Dependent Care Assistance Program (DCAP): funds elected for DCAP can be used for eligible dependent care expenses for qualified dependent(s) (as defined by IRS regulations) during the Plan Year and grace period. In order to be eligible, the expenses must be for the purpose of enabling you to work – for example, daycare expenses for a qualified dependent child under 13.

IMPORTANT: If you have questions about what constitutes a qualifying event for Flex Spending, whether a specific person would be considered a qualified dependent for you, or anything else pertaining to IRS regulations, please reach out to HR for clarification before you sign up.

How does Flex Spending work? If I enroll, when will I have access to my funds?

This depends on whether you enrolled in Healthcare Flex Spending and/or the Dependent Care Assistance Program (DCAP):

  • For Healthcare Flex Spending, you will have access to your full election for the year as of 1/1/2027. Funds will be deducted throughout the year on your biweekly paychecks. You will be provided with a payment card by our Flex Spending provider, TASC, and can use this card to pay for eligible expenses as you go. You can also submit receipts for reimbursement.
  • For DCAP, funds are made available only as money is added to the account; you will only have access to DCAP funds that have been deducted on your paychecks to date. You cannot use the TASC card for DCAP accounts, and will need to submit receipts for reimbursement.

Please see the Flex Spending memo on the Open Enrollment page for more details. The memo will be released on the first day of Flex Spending Open Enrollment.

Will I be automatically enrolled in Flex Spending for 2027 if I participated in 2026?

No. If you wish to participate in Flex Spending for 2027 (Healthcare Flex Spending and/or Dependent Care Assistance Flex Spending), you must actively (re)enroll via ESS during the Flex Spending Open Enrollment period.

It is also possible to enroll midyear if you experience an eligible qualifying life event. Please note that qualifying events for Flex Spending can differ from qualifying events for other insurance benefits.

If you are unsure whether a specific circumstance would be eligible, please reach out to the Benefits Team to inquire about this before submitting your election.

When does the grace period end for using up 2026 Flex Spending funds?

You will have until March 15, 2027 to incur claims against your 2026 FSA and DCAP funds and until March 31, 2027 to submit claims for expenses incurred through March 15, 2027.

Can I enroll in Flex Spending for 2027 via a paper or PDF form?

No. The only way to enroll in Flex Spending for 2027 is via the Employee Self Service (ESS) portal online. Any paper or PDF forms HR receives will be rejected.

Instructions for 2027 Plan Year Flex Spending enrollment via ESS will be provided on November 9.

I don't remember my ESS username or password. How do I log on?

Your ESS username is your MUNIS/City ID number and can be found on your paystub in the upper left-hand corner. HR or your Payroll Clerk can also confirm your ESS username for you. If you do not remember your password and/or are locked out of your account, please call IT at (608) 266-4193 to reset your password.

We strongly recommend you try to log on to ESS before the Flex Spending Open Enrollment period starts, or else early in the Open Enrollment period, to make sure you are able to access the portal.

IMPORTANT: ESS login also requires employees to answer two security questions (in addition to entering your password) for added security. It takes more time to reset your security questions than it does to reset your password. Because of this, we strongly recommend you do not leave your Flex Spending enrollment to the last minute, as if you need to reset your security questions, you may not receive a response in time to log in to ESS and submit your enrollment.

How do I decide whether to participate in the Healthcare FSA, and if so, what I should elect?

Neither HR nor Payroll can provide tax advice. If you have any questions about tax implications for electing either Healthcare FSA or DCAP, we recommend you speak with a tax professional.

You are the expert on your own situation. Typically, Healthcare FSA can be helpful if you are certain of your medical expenses in 2027. For example, because Healthcare FSA funds are made available as of January 1, Healthcare FSA can help offset the burden of paying for a large, planned, eligible expense, such as extensive dental work in 2027. Alternately, if you have regular, recurring expenses, such as monthly prescription costs, Healthcare FSA can allow you to set your predicted expenses aside pre-tax.

Several relevant considerations for Healthcare FSA elections

  • All expenses must be incurred during the Plan Year or grace period. If you incur an expense in December 2026 (for example, if your child gets braces in December), that is not an eligible expense for 2027 Flex Spending funds, as the expense was incurred before the start of the Plan Year on January 1.
  • IRS regulations govern Flex Spending maximums, parameters, limitations, and documentation requirements; employees are responsible for confirming their own eligibility for Flex Spending per IRS regulations.
  • If your spouse has a Health Savings Account (HSA) through their employer, you are ineligible to participate in Healthcare FSA per IRS regulations. (The City's plan does not include a limited-purpose Healthcare FSA.)
  • Some expenses require a Letter of Medical Necessity (LMN) in order to be eligible for Healthcare FSA. If you are unsure whether a given expense requires an LMN or not, please contact TASC.
  • It is not possible to move funds between Healthcare FSA and DCAP accounts.
  • Once the first payroll with your Flex Spending election has been processed, the election cannot be rescinded, even if you have made a mistake.
  • Flex Spending elections can only be amended midyear within 30 calendar days of an IRS-defined eligible qualifying event.
  • If you have funds remaining at the end of the year, it is possible to make qualifying purchases from the FSA store or similar IRS-compliant marketplaces.
  • Any funds remaining at the end of the grace period will be forfeit.

How do I decide whether to participate in DCAP, and if so, what I should elect?

Neither HR nor Payroll can provide tax advice. If you have any questions about tax implications for electing either Healthcare FSA or DCAP, we recommend you speak with a tax professional.

You are the expert on your own situation. Typically, employees who know they have qualified dependent(s) and an ongoing, stable childcare situation prefer to sign up for DCAP during Open Enrollment, as signing up during the Open Enrollment period ensures your DCAP election is divided equally between all paychecks in 2027, which lessens the financial burden on any given paycheck.

DCAP is also unique in that a change in the cost of daycare coverage is a qualifying event to increase (or decrease) your DCAP election midyear if you have an eligible dependent (per IRS regulations), depending on whether the cost change was an increase or decrease. There are also circumstances unique to DCAP under which it is possible to enroll in DCAP midyear (for example, a family member stops being able to care for your child and you need to start sending them to daycare to enable you to work).

IMPORTANT: if you are not sure whether you will have DCAP expenses at all, HR would recommend you do not enroll during Open Enrollment.

Several relevant considerations for DCAP elections

  • All expenses must be incurred during the Plan Year or grace period.
  • IRS regulations govern Flex Spending maximums, parameters, limitations, and documentation requirements; employees are responsible for confirming their own eligibility for Flex Spending per IRS regulations.
  • It is not possible to move funds between Healthcare FSA and DCAP accounts.
  • Once the first payroll with your Flex Spending election has been processed, the election cannot be rescinded, even if you have made a mistake.
  • Flex Spending elections can only be amended midyear within 30 calendar days of an IRS-defined eligible qualifying event.
  • DCAP is not for spouse/dependent medical expenses.
  • Any funds remaining at the end of the grace period will be forfeit.

How do I figure out who counts as a “qualifying person” or “eligible dependent” for Flex Spending?

Great question! This can get pretty tricky, as it’s dependent on IRS regulations. It is your responsibility as the individual to determine whether a given person’s expenses are eligible for your elected Healthcare FSA and/or DCAP funds. You may need to reach out to a tax professional or the IRS if you are unsure of eligibility; unfortunately, HR cannot give tax advice.

For Healthcare FSA: you can use Healthcare FSA funds for yourself, your spouse, and/or your qualifying dependent(s).

  • Child(ren) count as qualifying dependent(s) if they meet several criteria. Among these are that the child is under age 19 (or under age 24 if a full-time student) at the end of the calendar year – or any age if “permanently and totally disabled”; lives with you for at least half the year; and is dependent on you for at least half their support. Here’s more information from the IRS about qualifying children.
  • Healthcare FSA is individual, so if you and your spouse are both City employees, you can both elect up to the max for yourselves. Your individual expenses should not exceed the maximum.
  • If you are married and your spouse has an HSA through their employer, you are ineligible for Healthcare FSA. (The City's plan does not include a limited-purpose Healthcare FSA.)

For DCAP: you can use DCAP funds for expenses related to care for your child, disabled spouse, elderly parent, or other dependent who is physically or mentally incapable of self-care, so you (or your spouse) can work, look for work, or attend school full-time. Medical expenses are not eligible for DCAP reimbursement.

  • Child(ren) must be under age 13 when care was provided, and you must be able to claim a tax exemption for them (with one exception, outlined below).
  • There are special rules that apply to children of divorced or legally separated parents. In this circumstance, even if you cannot claim your child as a tax dependent they may still be treated as your qualifying person (rather than their other parent’s qualifying person) if you meet several criteria. More details are provided in the DCAP flyer and in the next question in this FAQ.

How does DCAP eligibility work if I'm divorced or legally separated?

TASC has confirmed the following about children of divorced or legally separated parents with regard to DCAP accounts, per IRS regulations (emphases added):

Even if you cannot claim your child as a dependent, they are treated as your qualifying person if all of the following are true:

  • The child was under age 13, or was not physically or mentally able to care for themselves.
  • One or both parents provided more than half of the child’s support for the year and are divorced, legally separated, or lived apart at all times during the last six months of the calendar year.
  • One or both parents had custody of the child for more than half of the year.
  • You were the child’s custodial parent. The custodial parent is the parent having custody for the greater portion of the calendar year. If the child was with both parents for an equal number of nights the parent with the higher adjusted gross income is the custodial parent.

A non-custodial parent who is entitled to claim the child as a tax dependent may not treat the child as a qualifying individual for the Dependent Care FSA, even when that parent is financially responsible for providing the care. Only one parent (the custodial parent) may qualify for the Dependent Care FSA benefit for a taxable year. The regulations do not provide any relief for a non-custodial parent that incurs dependent care expenses for the portion of the year in which they have custody of the child to enable the non-custodial parent to work.

Can DCAP be used for my spouse or child's medical expenses?

No. DCAP is not for dependent or spouse medical expenses – it is only for the cost of care for eligible dependent(s) that enables you to work, such as daycare expenses.

My spouse has an HSA through their employer. Am I eligible to enroll in Flex Spending?

If you are married and your spouse is enrolled in a Health Savings Account (HSA) through their employer - or if you have access to an HSA via a parent or a former employer - you are ineligible to participate in Healthcare Flex Spending through the City per IRS regulations. (The City's plan does not include a limited-purpose Healthcare FSA.)

You are still eligible to participate in Dependent Care Assistance Flex Spending (DCAP), but cannot enroll in Healthcare Flex Spending.

What is a Letter of Medical Necessity (LMN), and do I need one?

A Letter of Medical Necessity (LMN) is a signed letter from your medical provider that confirms a specific product/service is necessary for the diagnosis, treatment, or prevention of a medical condition. If a service or product requires an LMN, it is only eligible for Healthcare FSA reimbursement "when the expense is incurred to diagnose or treat a diagnosed medical condition," per IRS regulations.

Please note that IRS regulations govern when an LMN is required – not TASC policies. Additionally, because the IRS has been tightening its documentation requirements, some expenses that may not have required LMNs in previous years may now require LMNs.

  • A good rule of thumb is: if something could be prescribed by a doctor or could be obtained for personal use/general wellness, it's highly likely that an LMN will be required. Common examples include counseling/therapy, massage treatments, gym memberships, and vitamins/dietary supplements.

TASC has a template LMN that outlines all IRS-required information, and also includes additional details about when (and how often) to submit an LMN.

  • If you know that an expense will require an LMN, it's possible to complete the LMN ahead of time, so long as the LMN is specific to the Plan Year in question – that is, so long as it 1) specifies that it covers January 1, 2027 to December 31, 2027, and 2) outlines services to be received, the medical condition(s) the services are intended to treat, and the frequency of the service(s) within the Plan Year.
  • If you are unsure whether a planned expense requires an LMN or not, we strongly recommend you check with TASC and/or the IRS before you sign up for Healthcare FSA. Mis-estimating eligible medical expenses is not a qualifying event to change Healthcare FSA midyear.

Parking Account Benefit

New for 2027! Starting in 2027, the City will be offering a Parking Account Benefit to employees eligible for Flex Spending. A Parking Account enables you to contribute pretax dollars to pay for qualified work-related parking expenses.

How does the Parking Account Benefit work?

When you enroll in a Parking Account, you elect an annual contribution for the Plan Year based on your anticipated expenses and IRS limits. That election is deducted from your paycheck (before taxes) in equal installments throughout the year.

  • Please note that the deductions will be taken twice a month, which means they will not be taken on the two instances of a "third paycheck of the month" in 2027.

You will receive a TASC Card in the mail to use for eligible purchases. Simply swipe the card to pay for an eligible work-related expense, such as a parking ramp fee, and the funds are directly withdrawn from your available account balance. (Alternately, you can request reimbursement for an eligible expense via the TASC website or mobile app, or by using a paper form.)

  • If you are already enrolled in Flex Spending for FSA or DCAP, you would use your preexisting TASC card for the Parking Account Benefit.

Midyear changes can be made with an eligible midyear qualifying event, and impact future payroll deductions. Qualifying events for the Parking Account mirror qualifying events for DCAP. Reach out to the Benefits Team if you have any questions about this.

What can I use the Parking Account for?

Eligible expenses include:

  • Parking expenses incurred at work (meter, ramp) 
  • Work-related park-and-ride (expenses incurred at a location where you park and take public transportation to work)

Please note that gas, tolls, and ridesharing services are not eligible for the Parking Account Benefit. Additionally, it is your responsibility to maintain receipts that meet IRS substantiation requirements for all Parking Account claims.

Can I use the Parking Account with City parking structures?

Yes! You can definitely use the Parking Account for any work-related parking expenses at City lots/garages. Additionally, there are multiple City-run lots and garages that offer monthly parking permits. Monthly parking permit information is available on the Monthly Parking Permit page of the Parking Division website. 

Please note:

  • Different rates apply to Madison residents and non-residents.
  • Permits are a minimum 30-day agreement.
  • Be sure to save your receipts! All payment methods (online, in-person, etc.) will provide you with a receipt. It is your responsibility to maintain receipts that meet IRS substantiation requirements for all Parking Account claims.
  • For your expense to be reimbursable with the Parking Account, it must be incurred no earlier than January 1, 2027. If you pay a bill in December – even if that bill is for a parking reservation for January – it is not eligible for reimbursement with 2027 funds. You must pay the bill on or after January 1 for it to be a reimbursable expense for the Parking Account Benefit.
  • Waiting lists are maintained for all garage locations; permits are offered based on availability. The Monthly Parking Permit page linked above includes up-to-date details on which garages have availability. For more information, contact Monthly Parking at MonthlyParking@cityofmadison.com.

What else should I know about the Parking Account?

Please note:

  • Plan funds may only be used by the participating employee – expenses incurred by family members are not eligible.
  • Expenses must be incurred within the Plan Year to be eligible for reimbursement from the Parking Account. If you pay a bill in December – even if that bill is for a parking reservation for January – it is not eligible for reimbursement with 2027 funds. You must pay the bill on or after January 1, 2027 for it to be a reimbursable expense for the Parking Account Benefit.
  • Your contributions are subject to IRS limits. Learn more on the TASC website.
  • It is your responsibility to maintain receipts that meet IRS substantiation requirements for all Parking Account claims.
  • Contact Human Resources if you are unsure whether a given circumstance counts as a qualifying event!
  • Plan wisely – any funds remaining at the end of the year are forfeit.
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