I Got 5 Insurance Quotes in 22 Minutes (It Used to Take Me All Saturday)

The Saturday I lost to insurance forms

Last March, my car insurance renewal came in at $187/month. Up from $142. I did what any reasonable person would do: opened five insurance comparison sites in separate tabs and committed to getting quotes from all of them.

Three hours later, I had finished two quotes and rage-closed the third tab halfway through a form that asked for my VIN, every accident in the past 7 years, my daily commute distance in miles (not "short" or "long" but the actual number), and whether my car had anti-theft devices.

I never finished. Paid the $187.

That was $540 extra over the year because I could not stomach filling out three more forms. I think about that number a lot.

Why insurance forms are the worst forms on the internet

I have tested over 200 Chrome extensions and filled thousands of forms for reviews. Insurance quote forms are in a class of their own. Here is why:

• They are long. The average auto insurance quote form has 32 fields. Home insurance hits 40+. Health insurance enrollment can cross 50.
• They are multi-step. Most use 4 to 8 page wizards. Chrome autofill fills page 1. Pages 2 through 8 get nothing.
• They ask the same questions differently. One site says "Date of Birth." Another says "DOB (MM/DD/YYYY)." A third has three separate dropdowns for month, day, and year. Same information, three different formats.
• They use custom components everywhere. Custom date pickers, address autocomplete widgets, vehicle year/make/model cascading dropdowns. None of these are standard HTML that Chrome autofill can interact with.
• You need to fill out several to compare. One quote is useless. You need 3 to 5 to actually compare prices. That means typing your address, birthdate, SSN, and vehicle info 3 to 5 times. Nobody wants to do that.

The result? Most people do what I did. They start shopping, hit the wall of form fatigue, and just renew with their current provider. Insurers know this.

Insurance companies profit from form fatigue. Every quote you abandon is money they keep.

The experiment: 5 insurance quotes, timed

This year, I decided to try again. But this time I used an AI form filler to handle the repetitive typing. I picked 5 real insurance quote forms across different types:

1. Auto insurance (Progressive)
2. Home insurance (Lemonade)
3. Health insurance (Healthcare.gov marketplace)
4. Renters insurance (State Farm)
5. Life insurance (Haven Life)

I started a timer on each one. Stopped it when I hit the quote results page. Logged the field count, the number of pages/steps, and whether the AI needed any manual corrections.

Full transparency: I set up my Filliny profile with all my personal details, vehicle info, and property info before starting. That took about 3 minutes. I am not counting that in the times below because you only do it once.

Quote 1: Auto insurance (Progressive)

• Fields: 38
• Steps: 6 pages
• AI fill time: 4 minutes 12 seconds
• Manual corrections: 1 (selected wrong deductible tier)

Progressive's form is a 6-page wizard. Page 1 asks for address and date of birth. Page 2 is vehicle info with cascading dropdowns for year, make, and model. Page 3 is driving history. Pages 4 and 5 cover coverage options. Page 6 is the final review.

The AI handled all 6 pages, including the vehicle cascading dropdowns. It selected the correct year, then the make populated, then the model. The only miss was selecting a $500 deductible when I wanted $1,000. One click to fix.

Last year this form took me 18 minutes by hand. And I had to look up my VIN.

Quote 2: Home insurance (Lemonade)

• Fields: 29
• Steps: 1 long page (chat-style)
• AI fill time: 3 minutes 8 seconds
• Manual corrections: 0

Lemonade uses a conversational, chat-style interface instead of a traditional form. Questions appear one at a time. Chrome autofill cannot interact with this at all because each "field" is really a custom chat bubble component.

The AI treated each question as a form field and answered them in sequence. Property type, square footage, year built, security systems, distance to nearest fire station. Zero corrections needed.

This was the most satisfying one to watch. The chat-style interface that normally forces you to click through 29 individual questions just... filled itself.

Quote 3: Health insurance (Healthcare.gov)

• Fields: 47
• Steps: 8 pages
• AI fill time: 6 minutes 41 seconds
• Manual corrections: 2 (income estimate, tobacco use confirmation)

The big one. Healthcare.gov's marketplace application is 8 pages of household income, employer coverage questions, family members, and eligibility checks. 47 fields total, many of them conditional. If you say you have dependents, 12 more fields appear. If you have employer coverage, another 6.

The AI filled 45 of 47 correctly. It guessed my annual income as my profile's listed salary, which was last year's number. I had to update it. It also selected "No" for tobacco use, which was correct, but the site required me to manually confirm that answer with a separate checkbox. Weird UX, but not the AI's fault.

Six minutes and 41 seconds for a form that took me over 35 minutes last open enrollment. I had to dig through pay stubs, find my employer's EIN, and figure out what "modified adjusted gross income" means. The AI just pulled from my profile and filled.

Quote 4: Renters insurance (State Farm)

• Fields: 22
• Steps: 4 pages
• AI fill time: 2 minutes 49 seconds
• Manual corrections: 0

The easiest of the bunch. State Farm's renters form is shorter and more straightforward. Address, personal info, coverage preferences, payment. The AI breezed through all 4 pages.

One interesting thing: State Farm uses a custom address verification widget that pops up a "Did you mean..." confirmation after you type your address. The AI handled it. Chrome autofill would have filled the initial field but choked on the confirmation modal.

Quote 5: Life insurance (Haven Life)

• Fields: 34
• Steps: 5 pages
• AI fill time: 5 minutes 10 seconds
• Manual corrections: 1 (beneficiary relationship type)

Life insurance forms go deep into health history. Height, weight, medications, family medical history, hazardous activities. The AI filled my health details from my profile and correctly answered "No" to skydiving and scuba diving. (I am boring.)

The one correction: the beneficiary section asked for "Relationship" with options like "Spouse," "Child," "Parent," "Sibling," "Other." The AI selected "Other" instead of "Spouse." Not a huge deal but something to double-check. I filed a suggestion for this and I am told the matching for relationship dropdowns has been improved since.

The scoreboard: 22 minutes for 5 quotes

Total time across all 5 insurance quotes:

• Progressive (auto): 4:12
• Lemonade (home): 3:08
• Healthcare.gov (health): 6:41
• State Farm (renters): 2:49
• Haven Life (life): 5:10
• Total: 22 minutes flat
• Total fields filled: 170
• Manual corrections: 4 out of 170 (97.6% accuracy)

Compare that to my experience last year: 2 quotes in 3 hours, with the third one abandoned. That is roughly 90 minutes per quote manually versus 4.4 minutes per quote with AI assistance.

I should mention: the AI was not perfect. 4 corrections out of 170 fields. That is 97.6% accuracy, not 100%. You still need to review what it fills. But reviewing 170 pre-filled fields is a wildly different experience than typing 170 fields from scratch.

What the math looks like over a year

Stick with me on this because the numbers get interesting.

The average American household shops for insurance 2 to 3 times per year across auto, home, health, and life. Each shopping session should involve at least 3 quotes to get a meaningful comparison. That is 6 to 9 quote forms per year.

At 90 minutes per form manually: 9 to 13.5 hours per year spent on insurance forms.

At 4.4 minutes per form with AI: 40 to 60 minutes per year.

But the bigger number is the money you save by actually comparing. People who get 3+ quotes save an average of $400 to $900 per year on auto insurance alone, according to J.D. Power. The problem was never the comparison. It was the forms blocking you from making one.

You are not overpaying for insurance because you are lazy. You are overpaying because the forms are designed to exhaust you before you can compare.

Where the AI still needs a human

I would be lying if I said this was completely hands-off. Here is where I still had to think:

• Coverage amounts and deductible preferences. The AI fills based on your profile, but you might want different deductibles depending on the quote. I adjusted deductibles on 2 of the 5 forms.
• Income and financial fields. My profile had last year's income. I needed to update it for the health insurance application. This is a one-time fix.
• Unusual confirmation checkboxes. Healthcare.gov had a separate checkbox to confirm non-tobacco status even though the AI already answered the tobacco question. Edge case, but it exists.
• Ambiguous relationship fields. The life insurance beneficiary dropdown tripped up the AI once. These fields with context-dependent meanings are the hardest for any automated tool.

None of these took more than 10 seconds to fix. But I want to be honest about the experience. It is 97.6% automated, not 100%. If someone tells you any form filler is 100% perfect on insurance forms, they are selling you something. Or they have not actually tested it.

Tips for filling insurance forms faster

Whether you use an AI tool or type everything by hand, these tips will speed things up:

1. Have your VIN ready. Auto insurance forms almost always ask for it. It is on your registration card, insurance card, or the driver's side door jamb of your car. Save it somewhere you can copy-paste.
2. Know your property details. Home and renters forms ask for square footage, year built, roof type, and distance to nearest fire hydrant. Look these up once and save them.
3. Keep your health info current. Height, weight, medications, and family medical history come up in health and life insurance. Update your profile whenever something changes.
4. Open all quote sites in separate tabs first. Fill them in sequence. With an AI form filler, you can move through tabs quickly without losing momentum.
5. Always review before submitting. Whether AI-filled or hand-typed, wrong info on an insurance form can affect your quote or cause issues at claims time. The 30 seconds to review is worth it.

The security question (because someone always asks)

Insurance forms deal with sensitive data. SSN, income, health history. I get why people are cautious about using any tool with that information.

Here is what I checked before using Filliny on these forms:

• AES-256 encryption for stored profile data
• Does not store passwords or full credit card numbers
• Does not train AI models on user data
• Test mode lets you preview fills before committing
• Data stays on your device until a fill is triggered

I am not going to tell you to blindly trust any tool with your SSN. But I will say that typing your SSN into 5 different insurance websites manually is not exactly more secure. The data ends up in the same places either way. The question is whether you spend 22 minutes or 5 hours getting it there.

What I ended up saving

The original point of this whole exercise was to save money on insurance. Did it work?

My auto insurance renewal came in at $187/month again. After comparing all 5 quotes:

• Progressive: $164/month
• The one I switched to: $139/month
• Annual savings: $576
• Time spent: 22 minutes + 3 minutes initial setup

25 minutes of effort for $576 in annual savings. That is an effective hourly rate of $1,382/hour for the time spent. I will take that.

And that is just auto insurance. I have not finished shopping for home insurance yet. The Lemonade quote was promising.

How to try this yourself

If you are coming up on any insurance renewal, here is the playbook:

1. Install Filliny (free, 15 seconds, no credit card)
2. Set up a profile with your personal info, vehicle details, and property info. Be thorough. The more you put in, the fewer corrections you need later.
3. Open 3 to 5 insurance quote sites in separate tabs
4. Click the Filliny icon on each form. Review each page before clicking Next.
5. Compare your quotes and switch if the savings justify it

You get 5 free form fills without creating a paid account. That is enough to fill one complete insurance quote and see if the AI handles your specific forms. If you want to compare across 3 to 5 providers, the Pro plan runs about 27 cents a day. Less than a hundredth of what I saved.

Last year, form fatigue cost me $540. This year, 22 minutes of slightly supervised AI form filling saved me $576. I know which Saturday I prefer.