Pet Sitting Windsor

Book a pet sitter to stop by your home a few times a day to feed and play with your pet.

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Over 89
pet parents in Windsor have booked pet sitting

Windsor, Find top rated pet sitting

Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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Sitter Profile Image: Taryn E.
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Taryn E.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
• 39 reviews
18 repeat clients
4 years of experience
Windsor, WI, 53598

“Taryn was kind and very patient with my older, unsure little dog. Everyday Taryn took her time to get to know him. She was friendly and gentle allowing him to get used to her visits.”

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ZOE M.
Sitter Profile Image: Toni S.
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Toni S.
Star Sitter
from
$12
per visit
4.9 out of 5 stars
• 56 reviews
24 repeat clients
30 years of experience
DeForest, WI, 53532

“Toni went above and beyond! Not only did she take superior care of our little cavapoo, Bailey, she brought our garbage cans in from the curb and offered to check in on Bailey one more time if we were running late. Excellent care and service!!”

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Amy K.
Sitter Profile Image: Karen C.
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Karen C.
from
$15
per visit
5.0 out of 5 stars
• 6 reviews
1 repeat client
35 years of experience
Windsor, WI, 53598

“Karen did a excellent job caring for my cats! She followed all requests in a timely fashion. We arrived home to happy cats.”

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Mary Jo W.
Sitter Profile Image: Darshani L.
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Darshani L.
from
$13
per visit
5.0 out of 5 stars
• 4 reviews
1 repeat client
10 years of experience
Windsor, WI, 53598

“We had daily drop in visits with my dog and she was always there on time and gave Odin such great care. I would absolutely use her services again.”

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Ryan H.
Sitter Profile Image: Hailey M.
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Hailey M.
Star Sitter
from
$23
per visit
5.0 out of 5 stars
• 50 reviews
13 repeat clients
10 years of experience
Madison, WI, 53704

“Hailey was so great! Took such great care of my cat while I was away, couldn’t ask for better help. Very responsive and flexible with schedule that needed changing a few times. She sent pictures every drop-in and kept me updated! Definitely recommend Hailey to watch after your pets also.”

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Trevor S.
Sitter Profile Image: Maria & Bryan P.
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Maria & Bryan P.
from
$15
per visit
5.0 out of 5 stars
• 8 reviews
3 repeat clients
30 years of experience
Waunakee, WI, 53597

About: We have been loving and caring for dogs for a long time. Big and small dogs; young and old. Our son and 7 year old dog are welcoming I am currently working from home and Bryan works part time. Our son is home schooled at this time, therefore, we have time and energy to help other dogs and other families We have a large yard in a quiet neighborhood; part of our yard is fenced and other part is open for additional exercise. We also walk our dog daily.

Sitter Profile Image: Tina B.
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Tina B.
Star Sitter
from
$25
per visit
4.9 out of 5 stars
• 85 reviews
23 repeat clients
38 years of experience
Waunakee, WI, 53597

“I know I can always count on Tina to provide excellent care. We have three cats who are needy for attention and Tina always comes through with photos!”

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Morgan B.
Sitter Profile Image: Michelle H.
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Michelle H.
from
$20
per visit
5.0 out of 5 stars
• 4 reviews
2 repeat clients
23 years of experience
DeForest, WI, 53532

About: Lifelong (35 years) dog lover and owner of a golden retriever. I begged my parents growing up to get our family a dog...luckily after all of my persistence, my mom and dad finally gave in. My family got two dogs within a few weeks of one another, a Chocolate Lab and a Brittany. Both had a lot of energy and were very loving. Of course, the dogs came with the responsibilities which I happily took on. I loved taking them for walks, meal time, playing fetch in the yard, and even the poop scoopin' duties. Currently, I work from home and get to spend all day with my golden retriever Stark. I want to help the other working dog moms and dads in my community who don't have the luxury of being home with their dog every day. If you want help to take your dog out to go potty, go for a walk, snuggle, just visit, or play, then I'm the one for you!! I work from home and can be available as needed as long as it's not during a scheduled conference call - gotta keep my day job. I'm pretty flexible but also don't mind a routine schedule if that would benefit you. If any dog steps it's paws in to my home or yard, I'll treat them like a part of my own family. Just seeing a dog puts a smile on my face. I have a large home with wood floors. There's also a large nearby fenced-in dog park a few miles from my house where I take my golden retriever to really run off the zoomies. I love my dog and I'm obsessed with him. Every photo on my phone is of my dog, my kids, or food, the three loves of my life...oh and my husband, he's got a few photos in there too.

Sitter Profile Image: Kate H.
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Kate H.
from
$28
per visit
35 years of experience
DeForest, WI, 53532

About: There is not a breed that I won't work with. I believe all pets deserve love and affection and sometimes they need some extra care and that is great too. I am very flexible. This is my primary job and I can make any weekday work for visits and some weekends as well, I just need appropriate notice. I am open to any breed of cat or dog. I will follow any instructions you may have. My goal is to make your pet feel comfortable and happy.

Sitter Profile Image: Shatoria W.
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Shatoria W.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
• 38 reviews
13 repeat clients
10 years of experience
Madison, WI, 53718

“Shatoria was so great with my cats. She is very responsive and a great listener. I had a lot of changes in care instructions, and she handled everything patiently and without any issues. She kept me updated, followed all the details carefully, and made me feel completely at ease while I was away. I could tell my cats were well cared for and comfortable with her. I would absolutely trust her again and highly recommend her to anyone looking for a reliable and attentive pet sitter.”

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Duong H.
Sitter Profile Image: Rachel J.
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Rachel J.
from
$15
per visit
17 years of experience
Cherokee Park, Madison, WI, 53704

About: I grew up in a household with a minimum of us having 3 dogs at a time, ranging from 4 lb to 150 lb (shorkie/ irish wolfhound)! I'm a travel nurse in the area, and can't travel with pets, looking to spend some of my free time loving on animals. Along with having dogs growing up, we typically always had a cat or 2 to snuggle up with! I currently work 3 12 hours shifts in a week at the hospital. I do mostly night shift, however some day shifts. I typically have 4 days a week that I can spend watching your furry loved one! Since I am here on a travel nurse assignment, I am unable to watch your pet in my airbnb rental. This profile is for drop ins/ walking :)

Sitter Profile Image: Sarah W.
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Sarah W.
Star Sitter
from
$35
per visit
5.0 out of 5 stars
• 60 reviews
19 repeat clients
26 years of experience
Madison, WI, 53704

“Sarah as always took fantastic care of our cat while we were away for the holidays. Our cat is a chronic vomiter and as a result has a pretty strict food routine, and Sarah followed our instructions perfectly. She is always punctual, very communicative, and sends lots of photos. Our cat is clearly very happy and relaxed around her. I would recommend her to anybody!”

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Julia N.
Sitter Profile Image: Carley T.
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Carley T.
from
$21
per visit
5.0 out of 5 stars
• 12 reviews
6 repeat clients
20 years of experience
Sun Prairie, WI, 53590

“Carley is a delight and such a wonderful sitter! Incredibly sweet and a natural with animals, I had no worry at all leaving my pups in her care. Regular check-ins and photo updates throughout the weekend. I highly recommend Carley and will definitely try to book her again.”

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Suzanne S.
Sitter Profile Image: Mary W.
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Mary W.
from
$14
per visit
5.0 out of 5 stars
• 11 reviews
5 repeat clients
20 years of experience
High Crossing, Madison, WI, 53718

“Mary was communicative, asked questions, and gave excellent care for my dog. Thanks Mary! Will definitely book again.”

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Krista I.
Sitter Profile Image: Emma R.
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Emma R.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
• 9 reviews
2 repeat clients
10 years of experience
Sun Prairie, WI, 53590

About: I have experience fostering cats and dogs of all ages the last 6 years. I have experience with special needs dogs and cats, reactive dogs, and puppy training. I work from 7:30-4 Monday-Friday I am available to stay at the house to be there in the morning for the pets. I will be there right after work. I unfortunately cannot watch pets at my place, but I can stay at your place or can just stop by to feed and let out.

Sitter Profile Image: Kristina D.
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Kristina D.
Star Sitter
from
$22
per visit
5.0 out of 5 stars
• 8 reviews
2 repeat clients
20 years of experience
Waunakee, WI, 53597

About: Dogs are my favorite people - I attract dogs wherever I go. I have owned two dogs in my adult life-English Bulldog and Goldendoodle. Currently, I have a 10 year old goldendoodle. She loves everyone. I am a teacher and have off during the summer. I enjoy hiking, camping, biking, running, reading, gardening, and cooking. I’m currently on summer break, so my days are very flexible. During the school year, I am available before 7am or after 4pm. I have a very friendly goldendoodle. I have a big yard. I am willing to provide lots of love, playtime, and walks for your dog. I can be active with your pet or sit with them and love them up. Whatever you need, I can provide.

Sitter Profile Image: Emma W.
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Emma W.
from
$22
per visit
5.0 out of 5 stars
• 18 reviews
5 repeat clients
5 years of experience
Sun Prairie, WI, 53590

“Available on short notice! Lives close to my house and great with my big dogs! 10/10 would recommend!”

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Ashton O.
Sitter Profile Image: Heidi L.
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Heidi L.
from
$15
per visit
25 years of experience
Sun Prairie, WI, 53590

About: I've been caring for dogs and cats since I was a kid. Occasionally, for friends or neighbors, but most of my experience is from having a pups and cats of my own. I will be unable to adopt a dog for the foreseeable future, so this will be my way of staying connected to animals and making some new furry friends. I love spending time outside and I'm willing to head to the dog parks, trails or even the beach if you would like. Monay-Wednesday evenings are usually open. Most Fridays and Sundays I have more flexibility. Saturdays are also flexible if your pup/kitty is okay with kids. I have a daughter who loves animals as much as I do and she would be very gentle and playful. Every family and furry friend are different. That's one of the things I love about this job. I will be open to any specific routines, diets, training or requirements that you have in place.

Sitter Profile Image: Savannah T.
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Savannah T.
from
$19
per visit
5.0 out of 5 stars
• 5 reviews
1 repeat client
4 years of experience
Schenk-Atwood, Madison, WI, 53704

“Savannah did such an amazing job taking care of my fur babies! Even though I had only booked her for check-ins, she spent plenty of time playing with them and providing me with photos and updates daily!”

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Hannah G.
Sitter Profile Image: Madison & Alyssa F.
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Madison & Alyssa F.
from
$15
per visit
5.0 out of 5 stars
• 2 reviews
8 years of experience
Madison, WI, 53704

About: Hi! I’m Madison, a lifelong animal lover with hands-on experience caring for animals in both shelter and home settings. I volunteered with Shelter from the Storm Animal Rescue as a behavioral assessor, where I was trained to observe animal behavior, body language, temperament, and individual needs. I also helped write biographies for adoptable animals, which gave me even more experience getting to know animals as individuals and understanding their unique personalities. My family also fostered animals, so I’m very comfortable working with anxious, shy, fearful, or nervous pets. I understand that every animal is different, and some need extra patience and space before they feel comfortable with a new person. I pay close attention to body language, routines, comfort levels, and changes in behavior so I can meet your pet where they’re at and help them feel safe. I work a hybrid-remote job and am typically only in the office 1–2 days a week depending on my workload, which gives me a lot of flexibility with pet care. I love being able to spend extra time with pets who want companionship, playtime, enrichment, or just some good old-fashioned snuggles! My girlfriend, Alyssa, is also part of my pet-care journey as my partner in training! She is learning alongside me and may occasionally join me for pet care as she gains experience with different animals. I’ll remain the primary caregiver and point of contact throughout your booking. My goal is simple: I want your pets to feel safe, comfortable, loved, and well cared for while you’re away. I’ll take the time to learn their routines, respect their boundaries, and give them the individual attention they deserve. I work a hybrid-remote job and am only in the office 1–2 days a week depending on my workload, which gives me a lot of flexibility with pet care and allows me to spend extra time with pets who need more human interaction, playtime, or snuggles! Alyssa works second shift on weekdays, so depending on the timing of your booking, she may also be able to help fill in and spend time with your furbabies while I’m at work. I treat every pet and home with the same care and respect I would want for my own. I follow your pet’s normal routine as closely as possible, including feeding schedules, walks, medications, and any specific instructions you provide. My background as a trained animal behavioral assessor helps me recognize signs of stress, fear, discomfort, or overstimulation and adjust my approach accordingly. I’m especially comfortable with shy or anxious animals and will never force interaction before they are ready. I prioritize safe handling, secure doors and gates, and making sure pets cannot accidentally escape. I also respect your home by keeping things clean, following your instructions, and making sure everything is as you left it when I leave. Your pet’s safety and comfort are always my top priorities.

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The median cost per visit for pet sitting in Windsor is $20

Pet parents share their Rover experiences - Windsor

1 / 1
5.0 out of 5 stars

Taryn provided great care for our young cat! Multiple visits over a couple of days went great, and we would love to book with Taryn again.

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Christina P.
Drop-In Visits
5.0 out of 5 stars

Heather is the absolute best, most reliable sitter! She genuinely cares for our two senior boys and is so thorough with all their needs! She is a rockstar at giving medication and giving the both of them love. She goes above and beyond with the inconvenient tasks- taking care of the occasional puke and even washing up all their dishes. We trust her fully and will always go to her! ❤️

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Paige A.
Drop-In Visits
5.0 out of 5 stars

I feel sorry for those of you who did not find Brandy for your pet sitter, but lucky us!! She can never as far as I am concerned leave our family. Nemo is taken care of and watched over just as we would. Brandy lets you know if she has any concerns. For us we feel like our baby is sad we are gone but now when we come home he is right back to himself because he had great care while we were gone. This was an emergency booking and this time we did not leave her with any information and it was fine! THANK YOU BRANDY SO MUCH!

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Julie M.
Drop-In Visits
5.0 out of 5 stars

We had daily drop in visits with my dog and she was always there on time and gave Odin such great care. I would absolutely use her services again.

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Ryan H.
Drop-In Visits
5.0 out of 5 stars

Kelsey was great with our dog and his drop-in visits! I appreciated her flexibility with my visit time changes and her communication was awesome. I loved the pictures she included in her updates! Would definitely book her again

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Kristina J.
Drop-In Visits
5.0 out of 5 stars

Karen did a excellent job caring for my cats! She followed all requests in a timely fashion. We arrived home to happy cats.

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Mary Jo W.
Drop-In Visits
5.0 out of 5 stars

Peyton was awesome with our puppy Luna! She let us know what they did, kept us updated, and even took her for a walk during our drop in visit. Would recommend and have her come again!

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Jenna G.
Drop-In Visits
5.0 out of 5 stars

Tiana has done such a good job letting our puppy out for her lunch time breaks and walks!! We trust her completely and are so happy we found her!

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Jenna G.
Drop-In Visits
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  • Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
  • 24/7 support from the Rover team–here to help if you ever need someone to talk to.

Why Choose Rover?

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  • Reservation protection

    It doesn’t happen often, but if your sitter has to cancel, we’ll work with you to find a new sitter.

  • World-class support

    We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.

How to book pet sitting

  1. 1. Search

    Browse profiles of sitters near you who offer pet sitting.
  2. 2. Meet In Person

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Popular requests for pet sitting - Windsor

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Sitters in Windsor average 7
repeat pet sitting clients

FAQs for Pet Sitting - Windsor

Frequently asked questions about Rover

The average cost of Pet Sitting in Windsor is $17 per visit as of November 2026. Most bookings cost between $11 and $27 per visit. On Rover, sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.

As of November 2026, there are 1,461 sitters on Rover offering Pet Sitting across Windsor. Enter your ZIP code to see which available sitters are closest to your home.

You and your sitter can agree on a care schedule that fits your pet’s routine and the sitter’s availability. Pet Sitting can be booked as a one-time or recurring drop-in visit. If you need overnight care or dog walks, you may also be able to book House Sitting or Dog Walking through Rover with the same sitter, provided they offer those services.

Before booking, confirm:

  • the timing, length, and frequency of visits;
  • the care instructions the sitter should follow;
  • which parts of your pet’s usual routine should be prioritized;
  • how often you would like to receive messages, photos, or other updates.

Not every sitter offers the same services, availability, or booking options. Review their profile and discuss the care you need through Rover before booking each service.

If you would like updates while you’re away, you can discuss with your sitter how many or how frequent you’d like those updates to be. The Rover app allows sitters to send photos, videos, and messages about your pet, including how many pee or poop breaks occurred. You can message your sitter at any time through the app and our support team is available 24/7 by email or chat if you have concerns.

The personalized, in-home nature of pet care through Rover can mean more individual attention for your pet.

Many pet parents provide a spare key or arrange a lockbox. You can also exchange keys during the Meet & Greet and show your walker how to use digital fobs or personalized codes. It helps to arrange access to your home, from spare keys to concierge introductions, before pet care begins.

If you live in an apartment or condo, don’t forget to discuss details like buzzer access, codes, or elevator etiquette. These details can help a pet sitter feel more comfortable going in and out of your building.

Every sitter on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.

Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to $25,000 in eligible veterinary care. For more details, visit Rover's Trust & Safety page.

The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.

All bookings are backed by the Rover Guarantee, which provides up to $25,000 in eligible veterinary care reimbursement.

Yes, you can find sitters who have experience with handling special pet needs in Windsor. On Rover:

  • 89% of sitters can help with special care needs
  • 92% can help with giving oral medications or injections
  • 94% can help with daily exercise

You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.

Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.

A Meet & Greet is a casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.

Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your sitter interacts with your pet or the new environment.

During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your sitter questions about their skills and expertise, and make sure the fit feels right for everyone. Meet & Greets are a great way to prepare your pet and sitter for longer stays or first-time bookings. Read our tips for your first Meet & Greet.

sitters on Rover set their own cancellation policy, which you can find on their profile under their contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.

Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.

If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means you will get a full refund and our support team will work with you to find a replacement sitter.

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