House Sitting Chesterfield

Find a loving house sitter to watch over your pets and your home.

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Over 10
pet parents in Chesterfield have booked house sitting

Chesterfield, Find top rated house sitting

Prices are estimates per night for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.

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Sitter Profile Image: Janet M.
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Janet M.
Star Sitter
$62
total per night
4.9 out of 5 stars
17 reviews
7 repeat clients
53 years of experience
Chesterfield, MA, 01012

Janet did a great job with the pups and with the house. Janet sent photos every day and kept us informed as to how the dogs were fairing. Both the dogs and the house were in perfect condition when we returned home. Thank you so much!

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Allison M.
Sitter Profile Image: Paul J.
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Paul J.
$40
total per night
5.0 out of 5 stars
3 reviews
12 years of experience
Northampton, MA, 01053

About: I have cared and worked with cats and dogs since a young age. I will take my time to get to know your animals and they will trust and look forward to seeing me! I work as an educator, so my summer is open and super flexible. In July, I will be working from 8:30am - 12pm Monday through Thursday. Either way, I am a morning person. I love waking up and relaxing on the couch with the animals drinking some coffee or tea, and then spending the day on the couch or outside running around depending on their mood. I fully communicate with clients to ensure set boundaries and specific pet care needs. I can be hands on and active, or simply a presence in the room to ease anxiety.

Sitter Profile Image: Jaclyn P.
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Jaclyn P.
Star Sitter
$117
total per night
5.0 out of 5 stars
18 reviews
5 repeat clients
15 years of experience
South Deerfield, MA, 01373

Jaclyn knows the many moods and temperaments of dogs. Under the extraordinary confusion of a major home renovation project, she was able to settle our rescued pup upon arrival. We appreciated her excellent questions, skill, patience and forthright approach to leading him towards full exercise, calm homecomings and lots of fun in between. Thank you, Jaclyn!

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Eugenia C.
Sitter Profile Image: Kristin H.
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Kristin H.
Star Sitter
$84
total per night
4.9 out of 5 stars
28 reviews
11 repeat clients
3 years of experience
Northampton, MA, 01060

Kristin was a wonderful cat sitter who took great care of my two kitties while I was away. She was conscientious and communicative, sending updates and photos keeping me well informed of everything happening back home. Highly recommended!

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Stacey N.
Sitter Profile Image: Lori L.
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Lori L.
Star Sitter
$134
total per night
5.0 out of 5 stars
100 reviews
39 repeat clients
15 years of experience
Greenfield, MA, 01301

Lori is awesome. She watched our senior dog and our 2-year-old dog in our home for a week-long trip. She communicated very well and sent tons of pictures. She gave medications to our senior dog (who requires a lot of patience) and kept our younger dog well exercised. When our flight home got delayed, Lori was super understanding and flexible during the uncertainty. Our house was spotless when we got home. Lori is a true professional and we'd recommend her without hesitation. Thank you, Lori, for giving us peace of mind while we were away.

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Susan H.
Sitter Profile Image: Saige G.
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Saige G.
$56
total per night
4.9 out of 5 stars
35 reviews
13 repeat clients
11 years of experience
Easthampton, MA, 01027

Saige was amazing and took such great care of our fur baby. Isla is a 10 yo aussie shephard and full of energy and mischief. Saige was wonderful with her and I would HIGHLY recommend putting Saige's talents to work with your fur baby.

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julie s.
Sitter Profile Image: Jessica W.
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Jessica W.
Star Sitter
$89
total per night
5.0 out of 5 stars
16 reviews
7 repeat clients
30 years of experience
West Springfield, MA, 01089

Charlie had another great stay with Jessica. She was attentive to him, letting us know his chronic cough was increasing. She managed it well, professionally and patiently, with permission from us to give an extra dose of one of his medications. She communicated with us throughout the stay-

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Catherine D.
Sitter Profile Image: Alexis K.
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Alexis K.
$89
total per night
5.0 out of 5 stars
101 reviews
41 repeat clients
30 years of experience
Northampton, MA, 01053

Alexis fit in with all of our 4 leggeds and fish while we were on a week's vacation! She communicated daily, capturing our fur babies' pieceless interactions and some fishy facial expressions! Our home, inside and out, was well cared for. I highly recommend Alexis and would be happy to answer any specific questions. Having Alexis at the house took the stress away about leaving the house, mail, plants, garbage pick-up, deliveries, etc! Mark, Nala, and Tabor miss their roommate!

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Nancy D.
Sitter Profile Image: Alli Z.
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Alli Z.
$56
total per night
25 years of experience
Northampton, MA, 01062

About: I have always had at least 2+ dogs in my house since I was born. I currently have 2 of my own who make life so much better! I know it’s not always easy to work and have pets but I hope I can help some people no matter if it’s letting them out or walking them. I am currently a nurse but looking to also do house sitting, dog walking, drop ins, whatever is needed! I am available to help anytime after 4pm on weekdays and anytime on weekends! I am willing to go late as well! Some days I can also go before 7am I have two pets in my home one is a lab mix and one is a heeler mix. Both love all animals and people. They’re both three years old.

Sitter Profile Image: Fiona B.
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Fiona B.
$62
total per night
15 years of experience
Huntington, MA, 01050

About: My family owns and operates a Labrador breeding business and kennel, located in a small slice of heaven in the hill towns. I have been living, breathing, and loving dogs for my entire life and find immense joy simply being around them! I have several years of experience at a boarding facility where I was able to expand my knowledge on any different breed, size, age, temperament and disabilities! I am comfortable with all dogs at any life stages, ranging from a few hours old to sweet elderlies. I am also able to react quickly to any situation and have a solid history of preventing and intervening real fights safely between several dogs. I am available at you and your pets desire! I am able to stay in home and/or overnight, or simply check in! My car is my main way of travel, and has safely transported many pups to their playdates! Care in my clients home includes purely love and sticking to the routine that your pet knows the best! My client will also receive the utmost amount of reassurance and open communication because I understand on a personal level how difficult it is to leave your baby in someone else's hands.

Sitter Profile Image: Matt L.
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Matt L.
Star Sitter
$78
total per night
4.9 out of 5 stars
76 reviews
19 repeat clients
32 years of experience
Hadley, MA, 01035

I chose Matt because I had read his reviews and he lived up to the reputation! I think dogs are a good judge of character and she warmed up to him immediately upon his first visit to meet her. I had plans to leave the country and needed to feel like my pup was in good hands and well cared for. She has some special needs and Matt made sure she received the care she required. I loved the updates, pictures and videos Matt sent, all which helped me know she was happy and healthy. She even is jumping on people less! He somehow taught her to stop this annoying behavior and I need to find out how he did this!! I definitely would recommend him!

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Stacy P.
Sitter Profile Image: Sonya M.
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Sonya M.
$56
total per night
5.0 out of 5 stars
6 reviews
3 years of experience
Northampton, MA, 01060

Sonya cared for our dog and cat for a week in our home. She was easy to communicate with and great with both pets. Both animals and our house were in great shape when we returned from our vacation. I would absolutely hire Sonya again!

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Jane R.
Sitter Profile Image: Carol D.
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Carol D.
$40
total per night
4.9 out of 5 stars
40 reviews
9 repeat clients
30 years of experience
Sunderland, MA, MA, 01375

For almost 2 weeks, while I was on vacation in the EU, Carol was at my home with my dog and I was able to let go and completely enjoy my vacation because I knew my dog and home were in good hands. I would highly recommend Carol!

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Tracy M.
Sitter Profile Image: Carrie B.
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Carrie B.
$50
total per night
5.0 out of 5 stars
2 reviews
1 repeat client
10 years of experience
Northampton, MA, 01060

About: I’ve taken care of my family and friends dogs and cats. They have relied on me to feed, water, walk and occasionally give oral medication. I’m currently working up to 30 hours (4 days a week) over the summer while getting my masters at Smith College. I cannot afford to have a dog or cat of my own. I would love to be able give love to other peoples pets, it would be the best part of my day! I will make sure to take safety measures that are given/told to me very seriously. My #1 priority would be the safety of your pet!

Sitter Profile Image: Shawna B.
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Shawna B.
$76
total per night
5.0 out of 5 stars
9 reviews
4 repeat clients
15 years of experience
Westhampton, MA, 01027

Shawna provided wonderful care for our two small dogs who require overnight company. We are very satisfied with Shawna's level of care and would like to rebook her services in the future!

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Ray O.
Sitter Profile Image: Linda I.
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Linda I.
$67
total per night
5.0 out of 5 stars
3 reviews
20 years of experience
Hatfield, MA, 12057

My husband and I were leaving for our 10-day honeymoon when, just a week before our trip, our dogs virus acted up and he could no longer attend daycare as we had planned. We were so relieved to find Linda! She was incredibly communicative from the start and made herself available to lock everything in quickly, which gave us so much peace of mind before we left. While we were away, Linda sent us daily updates and photos of our pup, which we looked forward to every day. It was so reassuring knowing he was able to stay in the comfort of his own home and maintain his normal routine while Linda took such great care of both him and our house. Our 2.5-year-old Golden Retriever is full of energy, and Linda did an amazing job building a relationship with him and keeping him happy, active, and comfortable while we were gone. We came home to a happy dog and a well-cared-for home. We couldn't have asked for a better experience and would highly recommend Linda to anyone looking for a trustworthy, caring, and reliable dog sitter!

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Marissa N.
Sitter Profile Image: Julie G.
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Julie G.
$56
total per night
5.0 out of 5 stars
5 reviews
4 years of experience
Holyoke, MA, 01040

Julie was amazingly flexible, as our schedule was unknown, and was there when we needed her. More importantly, she was good with Ricky, took him out for walks as well as for his sanitary needs, and kept us regularly informed, with pictures. If we are in the area again we will seek her to assist us, and Ricky, again.

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John M.
Sitter Profile Image: Rose L.
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Rose L.
$74
total per night
5 years of experience
Goshen, MA, 01032

About: I’ve spent the last 5 years working in professional dog kennels in Berlin, MA, and I currently work at a local kennel here in western MA. During that time, I’ve cared for dogs of every size, age, and personality. From shy seniors who need gentle patience to high energy wiggle butts who never slow down. As a kennel supervisor, I’ve handled dogs with medical needs, administered medications safely and on schedule, and monitored behavior to keep every pup calm and comfortable. I’ve also been trusted to run the kennel independently, managing feeding routines, cleaning, enrichment, and safety from open to close. Now, I’m excited to bring that same level of professional, loving care into your home. Whether your dog needs a simple walk, extra patience, medication support, or someone who treats them like family, I’m here to make sure they feel safe, happy, and loved one walk, one wag, one kiss at a time. I just graduated from college and I’m working hard to save for my first home! This means I’m going to spend my days doing something I genuinely love, which is caring for pups. My schedule is flexible and I’m available almost every day of the week. I offer plenty of walking and drop‑in options throughout the week, and I’m always happy to work with you to find times that fit your dog’s routine. Whether your pup needs a quick potty break, a long walk, or some extra love while you’re away, I’m here to help. Availability: • Most weekdays: mornings, evenings, and some mid‑day slots depending on my kennel shifts • Weekends: flexible around my kennel shifts • Nearly every day available with advance request! Now that school is behind me, I’m able to take on more walks, drop‑ins, and extended care. I love what I do, and I’m committed to giving your pets reliable, loving, stress free care every single visit. <3 When I’m caring for pets in your home, my goal is to keep their routine as normal, comforting, and stress‑free as possible. I follow your instructions closely and make sure your pet feels safe, loved, and understood while you’re away. Here’s what you can expect: Routine‑Focused Care: I stick to your pet’s usual feeding, walking, play, and medication schedule so everything feels familiar and calm. Clear Instructions Welcomed: Written instructions, whether on paper or by text, are always helpful. I’m happy to follow detailed routines, special notes, or anything that keeps your pet comfortable. Open Communication: I keep communication easy and consistent. If anything comes up or you’d like updates, I’m always reachable and responsive. Photos Included: I send pictures and check ins so you can see how your furry family member is doing and feel connected while you’re away. Walks & Outdoor Time: I tailor every walk to what your dog enjoys, whether it’s relaxed neighborhood strolls, peaceful nature walks, or extra sniff‑time to burn off energy. Medication & Special Care: In my personal and professional experience, I am very comfortable with pets (cats or dogs!) who have medical conditions, including administering medications safely and on time (even insulin). Clean & Comfortable Spaces: I keep litter boxes clean, fluff up dog beds, refresh water bowls, tidy feeding areas, and make sure your pet’s space stays cozy and stress‑free. Behavior Awareness: With my kennel background, I’m trained to read body language and keep pets comfortable, especially shy, senior, or anxious animals. My goal is simple to make sure your pet feels safe, happy, and loved until you’re home again.

Sitter Profile Image: Dorjee D.
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Dorjee D.
Star Sitter
$73
total per night
5.0 out of 5 stars
28 reviews
16 repeat clients
15 years of experience
Amherst, MA, 01002

Dorjee provided one night of house sitting to care for my elderly cat and made herself available for periods of time throughout both days to spend time with her. Dorjee made sure food was eaten and consulted with me to figure out how to best give my cat her medication when she initially refused to take it. She clearly loves animals and taking care of them is a vocation.

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Madelyn F.
Sitter Profile Image: Erin O.
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Erin O.
Star Sitter
$78
total per night
5.0 out of 5 stars
36 reviews
10 repeat clients
20 years of experience
Westfield, MA, 01085

Erin did a great job taking care of our dog and house. Our dog was healthy and happy when we returned home and our house was exactly as we had left it. We hope Erin is available the next time we travel.

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Cynthia S.
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The median cost per night for house sitting in Chesterfield is $59

Pet parents share their Rover experiences - Chesterfield

1 / 1
5.0 out of 5 stars

Janet was absolutely wonderful. This was the first time I have had a stranger in my home caring for my dogs. (I usually have friends/family care for them). She was very loving towards my two dogs and sent me pictures daily. She took great care of my home and was tidy and overall a lovely person. I will be using her anytime I need dog care.

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Barra C.
House Sitting
5.0 out of 5 stars

Janet did a GREAT job caring for our girl, tons of walks amd company even with a 2ft snow blizzard during her stay. Kept the house amd took care of everything that came up too! Totally recommended!!

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Gordon A.
House Sitting
5.0 out of 5 stars

Sabrina was great with our high energy dog, and very communicative. I would definitely have her dogsit Petoskey again!

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Breana O.
House Sitting
5.0 out of 5 stars

Sabrina is AMAZING! This was her first time with our dog and Blue took to Sabrina right away. Incredibly thoughtful and kind and I will most definitely be requesting her again. Thank you!

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Dana K.
House Sitting
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  • Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
  • 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?

  • Cashless payments

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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.

Meet local sitters who will treat your pets like family

  1. 1. Search

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

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Sitters in Chesterfield average 4
repeat house sitting clients

FAQs for House Sitting - Chesterfield

Frequently asked questions about Rover

The average cost for House Sitting in Chesterfield on Rover is $41.07 per night (as of July 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of House 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 House Sitting. For more information on service fees, click here .

As of July 2026, there are 586 sitters on Rover offering House Sitting across Chesterfield. Enter your ZIP code to see which available sitters are closest to your home.

Beyond belly rubs and feeding schedules, a house sitter’s presence may provide an additional layer of security for your home. However, you will need to arrange overnight stays and other household tasks with your sitter when reaching out to them. Not all sitters offer the same services. Common household tasks you can negotiate include:

  • Mail & deliveries: Collecting letters and packages so they don't pile up.
  • Plant care: Keeping your indoor or outdoor garden hydrated.
  • Trash & recycling: Taking trash cans to the curb on scheduled pickup days.
  • Home security: Sitters can stay overnight to keep your home occupied.

The best way to align on expectations is during your free Meet & Greet. Use this time to provide a "home cheat sheet" that includes your preferred Chesterfield walking routes, the location of your favorite pet store, and any specific quirks about your home’s security or appliances.

It’s helpful to think of house sitting as a "home base" service. Most sitters in Chesterfield maintain their normal daily routines, like running errands or heading to the office, meaning your pet should be comfortable being alone for a few hours at a time. If your pet needs a little extra company, here is how to find the perfect match:

  • Look for "WFH" sitters: Many sitters mention "Work from Home" on their profile to indicate they’ll be present for the majority of the day.
  • Update your pet’s profile: Write down how long your pet can comfortably be left alone. This helps sitters quickly determine if their schedule aligns with your needs.
  • Communicate 24/7 needs: Standard house sitting usually doesn't include constant supervision. If your pet requires round-the-clock care, be sure to discuss this upfront.

Tip: Use the Meet & Greet to confirm a sitter's typical "away" windows. Transparency ensures your pet stays happy and your sitter can plan their day effectively!

Key handling is entirely up to you and your sitter to agree on during the Meet & Greet or in the Rover app. Most pet parents in Chesterfield choose to hand over a spare key or digital fob in person, while others arrange a lockbox or unique access code. Don't forget to discuss key returns as well!

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.

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 .

If a health concern arises during a stay, your sitter is instructed to contact you and our Trust & Safety team immediately and, if needed, take your pet to the closest veterinarian. Through our Trust & Safety support team, sitters can ask for diagnostic advice from a qualified veterinary professional if your pet is showing signs of possible illness.

For extra peace of mind, you can also prepare an authorization form for your regular vet. An authorization form outlines your preferred method of care and allows your sitter to bring your pet into their regular clinic.

Every qualified booking made on Rover is backed by the Rover Guarantee, which includes reimbursement for eligible emergency vet care.

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.

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

  • 94% of sitters can help with special care needs
  • 100% 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.

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