Pet Sitting Chesapeake City

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 54
pet parents in Chesapeake City have booked pet sitting

Chesapeake City, 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: Lexis I.
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Lexis I.
from
$15
per visit
14 years of experience
Middletown, DE, 19709

About: I have cared for and loved all range of animals from dogs, cats, and rodents! I have been caring for animals since I was 10 years old for family and friends. I can work with all dog breeds and sizes as I have personally owned and cared for all kinds from chihuahuas to cane corsos! Cats have always been a pet of mine as well and cared for multiple family members felines. I currently assist in fostering dogs and took up dog trainings for a few years. I’m currently working full time - however - I spend my evenings caring for my foster dog and in the weekends I will do drop ins for a family or neighbors hospice pet. I have a fenced in yard as well as a large variety of food for certain nutritional diets depending on the foster dog at that time. I ensure safe environments to ensure the animal is in the best care and comfortability.

Sitter Profile Image: Destiny P.
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Destiny P.
Star Sitter
from
$30
per visit
5.0 out of 5 stars
107 reviews
21 repeat clients
10 years of experience
Bear, DE, 19701

Destiny is AMAZING! After having to cancel a horrible dog sitter she immediately stepped up to help. My dog absolutely loves her! She is a 10/10 and will always try to book with her first!

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D.j. W.
Sitter Profile Image: Aleisha T.
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Aleisha T.
from
$20
per visit
5.0 out of 5 stars
4 reviews
5 repeat clients
15 years of experience
Chesapeake City, MD, 21915

Aleisha is so great! She took the time to meet our dogs ahead of time and get the lay of our house. She manages all 4 of our pups with ease! Our dogs range from puppy to senior, and she takes good care of all their individual needs. She is always on time and so flexible with our changing schedules. She communicates everything and takes the best pics during her visits! Book her now :)

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Erica W.
Sitter Profile Image: Brice B.
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Brice B.
from
$15
per visit
5.0 out of 5 stars
7 reviews
1 repeat client
14 years of experience
Newark, DE, 19702

About: I’ve grown up in a home with dogs, and worked briefly in an animal shelter, caring for dogs from newborn puppies to seniors, responsible for their daily care and enrichment. My shifts are short consistent, allowing me to have a concrete schedule to work around to best meet the needs of all dogs and cats. As the seasons change, so do my hours, allowing me more availability for bookings. I have knowledge on animal enrichment and training, and know how to handle different pets with all different temperaments. I know how to crate dogs, walk them, and bond with all sorts of dogs and cats.

Sitter Profile Image: Paul C.
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Paul C.
from
$20
per visit
5.0 out of 5 stars
6 reviews
1 repeat client
10 years of experience
Elkton, MD, 21921

Love the photos! This was our first time using anyone for a pop in visit. This was totally last minute! Asked Paul and his fiance last night at 7pm to please help us, and without hesitation they came right over and met our boys. They did a pop in visit today and they were wonderful!!! Will definitely use them again :) They were great!!!! Thank you both so much !

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Leanna
Sitter Profile Image: Kelsie T.
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Kelsie T.
from
$25
per visit
5.0 out of 5 stars
10 reviews
3 repeat clients
15 years of experience
Elkton, MD, 21921

About: Hi there! My name is Kelsie, and caring for animals isn’t just something I do—it’s who I am. With over 15 years of both professional and personal pet care experience, I bring a deep understanding of animals of all kinds and the love they deserve. I’m comfortable caring for a wide variety of pets, from dogs and cats to birds, fish, and small animals. In fact, my own home is full of furry (and feathery!) family members—I currently have four dogs, a bird, a fish, and a chinchilla. Because of this, I’m very familiar with different temperaments, routines, and care needs. Whether your pet is a playful puppy, a senior who needs extra patience, or has medical needs that require special attention, you can trust that they’ll be in capable and compassionate hands. I have experience caring for pets of all ages and am attentive, reliable, and detail-oriented when it comes to following care instructions. Your pet’s safety, comfort, and happiness are always my top priorities. I treat every animal like they’re my own and strive to make sure they feel loved and secure while you’re away. I’d love the opportunity to meet you and your pet! I have a busy schedule but I always make time for my clients and their pets. And they always have my focus while I am spending time with them. My husband helps me with my services and between the two of us someone is almost always home! I believe that care should be tailored to each specific pet, so I do not have a set care plan until I meet you and your pets

Sitter Profile Image: Reid C.
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Reid C.
Star Sitter
from
$62
per visit
5.0 out of 5 stars
68 reviews
18 repeat clients
24 years of experience
Glasgow, DE, 19702

Our 3rd time booking with Reid- great as always! Provided pictures and played with our dog outside! Will continue to book Reid whenever we need dog coverage!

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Kelly G.
Sitter Profile Image: Nancy L.
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Nancy L.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
12 reviews
2 repeat clients
12 years of experience
Newark, DE, 19702

About: I’ve spent years caring for and training dogs, including raising and training four Australian Cattle Dogs—a breed known for its intelligence and high energy. Through that experience, I’ve learned how to read canine body language, reinforce good behaviors, and confidently handle dogs with different personalities and energy levels. I’ve also walked dogs for several of my mom’s clients throughout the Hockessin and Wilmington area. My focus is on providing safe, reliable, and personalized care while treating every dog as if they were my own. I am home full-time, which allows me to provide attentive, personalized care throughout the day. Your dog won’t be left alone for long periods and will receive plenty of potty breaks, exercise, playtime, enrichment, and affection. Being home full-time also allows me to closely monitor each dog’s well-being, maintain their routine, and ensure they feel safe, comfortable, and loved while you’re away. Your dog will be cared for like one of my own in a safe, loving home environment. I have a fully fenced 0.6-acre yard where dogs can safely run, play, and explore under supervision. They’ll also have the companionship of my three friendly, well-socialized dogs if they enjoy being around other dogs. Throughout the day, your pet will receive plenty of exercise, potty breaks, playtime, enrichment, and affection. I follow each dog’s routine as closely as possible, including feeding schedules, medications, and any special instructions, so they feel comfortable, happy, and at home while you’re away.

Sitter Profile Image: Nikkita J.
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Nikkita J.
Star Sitter
from
$19
per visit
5.0 out of 5 stars
51 reviews
19 repeat clients
4 years of experience
Middletown, DE, 19709

Nikkita was perfect. We needed a walker same day with very little notice and she came through to walk our boy. She was very sweet and communicated everything with us. We would definitely use her again.

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Dan R.
Sitter Profile Image: Meredith V.
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Meredith V.
from
$15
per visit
1 repeat client
20 years of experience
Newark, DE, 19702

About: I have grown up around dogs my entire life, big and small! I’ve bathed, feed, played with, and let dogs outside! Cuddles are a must! I attend Western Kentucky University but am home for the summer. I currently work part time at Brusters Ice Cream! My schedule changes weekly however I don’t work everyday meaning there is plenty of time for stopping by throughout the day! I will update clients on schedule changes to fit their needs and make sure all pets are taken care of properly. Most shifts are at night so I can stop by for feedings and bathroom breaks before work and after! Care begins with attention. Following clients instructions as every dogs and cats needs are different. Proper safety, comfort, and routine is important! Whether backyards aren’t fenced in or animals are fed at a specific time clients instructions are always important to follow!

Sitter Profile Image: Christine S.
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Christine S.
Star Sitter
from
$17
per visit
5.0 out of 5 stars
29 reviews
16 repeat clients
25 years of experience
Elkton, MD, 21921

Couldn’t be happier with Christine and how she took care of our three fur babies. Each one has a very unique personality and two out of three need to be won over which Christine did quickly. Her checks-ins were both full of information and very thoughtful with lots of pictures showing how well they were behaving while we were away. We will definitely use Christine again.

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Renae K.
Sitter Profile Image: Breanna P.
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Breanna P.
from
$22
per visit
5.0 out of 5 stars
57 reviews
19 repeat clients
16 years of experience
Middletown, DE, 19709

Breanna was amazing with Maggie! She was very communicative, spent quality time with her and took her on walks. She even brought her dog over to play with Maggie and I thought that was awesome! I would definitely recommend Breanna anytime and I know that we will be asking her again, if we need a sitter in the future!

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Angela S.
Sitter Profile Image: Courtney B.
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Courtney B.
from
$20
per visit
10 years of experience
Bear, DE, 19701

About: I’ve grown up with dogs my whole life. I adopted a cat two years ago & can confidently say I now know the difference between how to interact with both. My friends call me the cat whisperer & I’ve watched both cats & dogs before. I am available to pet sit weekdays. My availability does depend on the week- I work remote so I am more flexible. I will try to keep my posted schedule as up to date as possible. I care for every pet with compassion & love. I understand that every dog/cat is different & needs to be treated accordingly. I get the importance of knowing your pet is safely looked after & treat them like my own.

Sitter Profile Image: Hailey G.
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Hailey G.
from
$16
per visit
5 years of experience
Newark, DE, 19702

About: I’ve always taken care of pets from the age of 10, whether my own or family and friends. I enjoy spending time with pets and make it my mission to fulfill their day with their needs and wants. My favorite part of getting to pet sit is the cuddles and play time of course as well as getting to know each and every pet’s personalities. I’m currently working part-time as well in school part-time, my availability for Tuesdays and Thursday are anytime from 2pm-10pm due to school. Friday and Saturday I am available anytime from 10am-8pm, plenty of time to play and cater to your pets! I do not have the environment to pet sit at my home, but am willing to travel to care for your pets! I take all precautionary measures and follow instructions to the T to ensure your pets needs are met and to your standards. I aim for being responsible yet sprinkling in some fun.

Sitter Profile Image: Yvonne & Joseph K.
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Yvonne & Joseph K.
Star Sitter
from
$30
per visit
5.0 out of 5 stars
190 reviews
47 repeat clients
50 years of experience
Newark, DE, 19702

Highly recommend booking with Yvonne. She is always on time. Takes great pictures of Ky. He enjoys hanging out with her and is always excited to see her arrive. Yvonne is very friendly and I never feel like I have to worry about Ky while he’s in her care!

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Leticia W.
Sitter Profile Image: Stephanie J.
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Stephanie J.
from
$18
per visit
5.0 out of 5 stars
87 reviews
17 repeat clients
20 years of experience
Warwick, MD, 21912

Stephanie was such a life saver this week! I needed assistance with my puppy & she was incredibly flexible and able to meet my needs! Stephanie is a fantastic communicator, provides ample detail and photos about her visit & such a sweet and patient caregiver! Thank you so much! Dutton looks forward to seeing you again soon!

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Emily C.
Sitter Profile Image: Brittany F.
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Brittany F.
from
$15
per visit
5.0 out of 5 stars
11 reviews
20 years of experience
Warwick, MD, 21912

About: My farm is a beautiful sanctuary that we love to share with all furry friends! Whether they want to splash in the pool, run outside in a safe CLEAN secure area, or just have a nice snuggle in their indoor kennel or maybe even stretch out on the couch- just know they’ll be wagging to come back! I have 6 horses on the property, 13 chickens, 2 turkeys, 2 outdoor barn cats, and my Friendly Laid back dog Archie. I provide love & care which is more important than anything else. But of course- I follow parents rules! My entire life revolves around my farm and caring for all of my animals. I am on the property 24/7 as this is my full time job. And luckily it’s my passion. We have a beautiful fenced in pasture with lots of space to run. We are in a very private and rural area. We also have a pool- only if parents are OK and the Pup chooses to take a dip! Your Pup will always be supervised. If there are restrictions we will always abide by them. We also have dog crates if needed or requested and a beautiful inside area as well. Basically your Pup is gonna have free range and feel a home away from home.

Sitter Profile Image: Tre S.
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Tre S.
from
$25
per visit
4.6 out of 5 stars
14 reviews
2 repeat clients
6 years of experience
Middletown, DE, 19709

Tre is on time and communicates all about the visit. He is extremely professional and easy to work with. Plus my dog did not bark at him!!! While my Bella has fears and anxiety issues, he found ways to work with her. We will definitely use him again!

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Judie B.
Sitter Profile Image: Randall D.
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Randall D.
from
$15
per visit
12 years of experience
Middletown, DE, 19709

About: As an engineer and proud owner of two large dogs, I bring attention to detail, and reliability to pet care. I am organized, observant, and proactive, ensuring every walk, meal, and play session is safe, structured, and enjoyable. With years of hands-on experience caring for my own dogs, I carefully observe behaviors, anticipate needs, and provide personalized love and attention, giving each pet a happy, and secure experience. I am a full-time Engineer working a 4-10 schedule where I am off 3 days per week. I have plenty of time to take care of pets during the weekends. I have 2 dogs that are extremely well behaved and friendly. They are both crate trained and love to play in the fenced in backyard.

Sitter Profile Image: Melissa J.
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Melissa J.
from
$25
per visit
4.8 out of 5 stars
12 reviews
3 repeat clients
41 years of experience
Middletown, DE, 19709

About: I have always had pets. As a toddler my dog and I would explore the woods together. I have had pet birds, fish, hamsters, turtles, spiders, frogs, lizards, rabbits, horses, turkeys, chickens, cats and dogs. I also have experience caring for cows and sheep. I started doing pet care professionally as a teen. I eventually started training dogs as well. I did that until I moved for college. Now, I started providing those services in my home. Having dogs stay with me gives me the opportunity to provide 24/7 care and training. I trained my last dog to be a hearing dog. She always alerted me to the door and phone, so I incorporated those natural likes and abilities into her training. I'm currently preparing my new dog for search and recue training based upon his love of playing hide and seek. All dogs have their own natural abilities and like different things. I have used clicker training in the past. I usually use reward based training. I occasionally seperate dogs, so they might not play together unless they are from the same household. I have rooms set up as individual dog suites. I have lots of cozy blankets and toys for dogs to feel comfortable. Dogs will still roam and play throughout the house. Dogs will get lots of individual attention. Dogs usually make friends and enjoy playing together. There are lots of toys beds and blankets for them to get cozy and have fun. I have a large unfenced yard (will be fully fenced in October. Currently only one side is fenced.) that backs to woods with a creek and a park. Dogs will be leashed outside. I can take more than one dog and for extended stays. Dogs should bring their own food and potty training pads if they use them. I send lots of pictures of your dogs during their stay. I can send videos and have done live chat videos, so you can see and talk to your dog. Dogs will be taken outside regularly. Dogs will go outside in all weather at least 2 times during the day. Dogs also will have ample play time indoors with running, chasing, fetching or jumping. Dogs can play ball or nap. I take dogs running at the park. Each dog will be cared for according to his personality. Dogs get alot of individual attention. I make sure dogs are comfortable throughout the day and i play with them and incorporate them into my day as much as possible. My 2.5 year old son and husband also play with the dogs. They help train, feed and care for dogs too. They also run with dogs and take them to the park or dog park. Dogs may go to the store with us or on errands or on an outing. Dogs may sleep in our bed with us. Dogs may join in for Disney songs and dancing. Dogs may make new friends and bond. I only care for a few dogs at any given time. I can care for dogs weekly and monthly. I can cater to dogs special or individual needs. Drop off pick up is between 6am to 7am or 7pm to 8pm weekdays and anytime weekends. More About Me: I started pet care professionally more than 20 years ago, when i was studying nursing. I was in college and nursing school full time, working at a healthcare facility full time, doing home care and pet care. I received both of my undergraduate degrees in legal studies. I started 2 master's degree programs one in law and one in business. I plan to continue doctorate studies in psychology. My main interest is behavior. My other interests are sociology and anthropology. I also write. I love dog care. It's fun! Even when the work is hard, it's rewarding. I'm glad i decided to focus on dog care again. My days are much better with dogs in my life. More About My Family: My son has benefited from having dogs in his life and it has afforded him an early opportunity to begin working with animals. My son is an animal lover. He especially loves dogs. He's a good trainer and pet care provider. He has a deep concern for dog's feelings and goes out of his way to see them happy. He likes taking care of animals, especially dogs. He's interested in going to school, so he can learn more about taking care of animals. My husband loves dogs. He grew up with dogs and cared for additional dogs. He has a relaxed natural approach and does not use training as much as treats play and petting.

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

Pet parents share their Rover experiences - Chesapeake City

1 / 1
5.0 out of 5 stars

Aleisha is so great! She took the time to meet our dogs ahead of time and get the lay of our house. She manages all 4 of our pups with ease! Our dogs range from puppy to senior, and she takes good care of all their individual needs. She is always on time and so flexible with our changing schedules. She communicates everything and takes the best pics during her visits! Book her now :)

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Erica W.
Drop-In Visits
5.0 out of 5 stars

Aleisha did a great job taking care of our 4 dogs. There are varying needs from care for an aging dog to younger energetic ones. They all seemed very happy.

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Kathryn H.
Drop-In Visits
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Sitters in Chesapeake City average 6
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FAQs for Drop-In Visits - Chesapeake City

Frequently asked questions about Rover

The average cost for Pet Sitting in Chesapeake City on Rover is $17.76 per visit (as of August 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of Pet Sitting easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for Pet Sitting. For more information on service fees, click here .

As of August 2026, there are 1,888 sitters on Rover offering Pet Sitting across Chesapeake City. Enter your ZIP code to see which available sitters are closest to your home.

A pet sitter can provide focused care sessions, help your pet’s routine stay on track, or keep you updated on your pet’s mood and energy levels.

Whether you’re at the office for the day or traveling for a few nights, a pet sitter can offer potty breaks during a Chesapeake City stroll, cleaning the litter box, or making sure your pet has on-time food or water refills. For daytime services like walking and drop-ins, you can also request sitters to send a report card with every visit.

Tip: You can discuss your specific arrangements with a pet sitter on Rover to what fits you, your pet, and your sitter’s needs. To find what their special skills are, look at the "Skills" and "Pet care experience" sections on their profile.

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 Chesapeake City. On Rover:

  • 95% of sitters can help with special care needs
  • 95% 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 short introductory meeting between you, your pet, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter 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. Most pet parents and sitters on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.

Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.

Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.

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

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