Used 2020 Jeep Cherokee for Sale nearWindsor, ON
- Year:
- 2021
- Make:
- Jeep
- Model:
- Cherokee
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 180 hp 2.4L I4
- Exterior colour:
- Silver
- Combined gas mileage:
- 10 L/100km
- Fuel type:
- Gasoline
- Interior colour:
- Black
- Transmission:
- Automatic
- Mileage:
- 155,529
- Stock #:
- 35309
- VIN:
- 1C4PJMMX9MD136393
Sponsored by Stockie Chrysler Dodge Jeep Ram
2021 Jeep Cherokee
Altitude 4WD
155,529 km
$19,499
- Year:
- 2019
- Make:
- Jeep
- Model:
- Cherokee
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 271 hp 3.2L V6
- Exterior colour:
- Black
- Combined gas mileage:
- 11 L/100km
- Fuel type:
- Gasoline
- Interior colour:
- Black
- Transmission:
- Automatic
- Mileage:
- 147,738
- Stock #:
- 374664
- VIN:
- 1C4PJMDX2KD374664
-$1,000
Sponsored Listing
2019 Jeep Cherokee
Limited 4WD
147,738 km
$17,990
$16,990
- Year:
- 2020
- Make:
- Jeep
- Model:
- Cherokee
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Exterior colour:
- Black
- Interior colour:
- Black
- Transmission:
- Automatic
- Mileage:
- 114,490
- Stock #:
- 7697
- VIN:
- 1C4PJMBN3LD553766
Sponsored Listing
2020 Jeep Cherokee
Trailhawk 4WD
114,490 km
$21,599
- Year:
- 2019
- Make:
- Jeep
- Model:
- Cherokee
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 271 hp 3.2L V6
- Exterior colour:
- Red
- Combined gas mileage:
- 11 L/100km
- Fuel type:
- Gasoline
- Interior colour:
- Black
- Transmission:
- Automatic
- Mileage:
- 106,221
- Stock #:
- 31810
- VIN:
- 1C4PJMDX2KD415469
2019 Jeep Cherokee
Limited 4WD
106,221 km
$16,999
- Year:
- 2019
- Make:
- Jeep
- Model:
- Cherokee
- Body type:
- SUV / Crossover
- Engine:
- 271 hp 3.2L V6
- Exterior colour:
- White
- Fuel type:
- Gasoline
- Interior colour:
- Black
- Transmission:
- Automatic
- Mileage:
- 92,643
- Stock #:
- 260638A
- VIN:
- 1C4PJMCX4KD274003
2019 Jeep Cherokee
92,643 km
$19,199
- Year:
- 2021
- Make:
- Jeep
- Model:
- Cherokee
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 271 hp 3.2L V6
- Exterior colour:
- Green
- Combined gas mileage:
- 11 L/100km
- Fuel type:
- Gasoline
- Interior colour:
- Black
- Transmission:
- Automatic
- Mileage:
- 77,000
- Stock #:
- MD128305
- VIN:
- 1C4PJMCXXMD128305
2021 Jeep Cherokee
80th Anniversary 4WD
77,000 km
$24,498
- Year:
- 2021
- Make:
- Jeep
- Model:
- Cherokee
- Body type:
- SUV / Crossover
- Exterior colour:
- Red
- Transmission:
- Automatic
- Mileage:
- 145,563
- Stock #:
- MD146544P
- VIN:
- 1C4PJMBX6MD146544
2021 Jeep Cherokee
Trailhawk Elite 4WD
145,563 km
$20,499
- Year:
- 2019
- Make:
- Jeep
- Model:
- Cherokee
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 270 hp 2L I4
- Exterior colour:
- Black
- Combined gas mileage:
- 11 L/100km
- Fuel type:
- Gasoline
- Interior colour:
- Black
- Transmission:
- Automatic
- Mileage:
- 123,385
- Stock #:
- B5018
- VIN:
- 1C4PJMBN6KD223568
2019 Jeep Cherokee
Trailhawk Elite 4WD
123,385 km
$17,663
- Year:
- 2019
- Make:
- Jeep
- Model:
- Cherokee
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 271 hp 3.2L V6
- Exterior colour:
- Black
- Combined gas mileage:
- 12 L/100km
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 92,061
- Stock #:
- KD447167
- VIN:
- 1C4PJMBXXKD447167
2019 Jeep Cherokee
Trailhawk 4WD
92,061 km
$18,999
- Year:
- 2021
- Make:
- Jeep
- Model:
- Cherokee
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 271 hp 3.2L V6
- Exterior colour:
- Black
- Combined gas mileage:
- 12 L/100km
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 162,375
- Stock #:
- 4622
- VIN:
- 1C4PJMBX6MD117822
2021 Jeep Cherokee
Trailhawk 4WD
162,375 km
$15,999
- Year:
- 2019
- Make:
- Jeep
- Model:
- Cherokee
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 271 hp 3.2L V6
- Exterior colour:
- White
- Combined gas mileage:
- 11 L/100km
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 47,512
- Stock #:
- KD467123P
- VIN:
- 1C4PJMDX6KD467123
2019 Jeep Cherokee
Limited 4WD
47,512 km
$21,699
- Year:
- 2019
- Make:
- Jeep
- Model:
- Cherokee
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 271 hp 3.2L V6
- Exterior colour:
- White
- Combined gas mileage:
- 12 L/100km
- Fuel type:
- Gasoline
- Interior colour:
- Black
- Transmission:
- Automatic
- Mileage:
- 162,305
- Stock #:
- (3-16) 160903
- VIN:
- 1C4PJMBX5KD160903
2019 Jeep Cherokee
Trailhawk 4WD
162,305 km
$15,798
- Year:
- 2019
- Make:
- Jeep
- Model:
- Cherokee
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 271 hp 3.2L V6
- Exterior colour:
- Black
- Combined gas mileage:
- 11 L/100km
- Fuel type:
- Gasoline
- Interior colour:
- Black
- Transmission:
- Automatic
- Mileage:
- 147,738
- Stock #:
- 374664
- VIN:
- 1C4PJMDX2KD374664
-$1,000
2019 Jeep Cherokee
Limited 4WD
147,738 km
$17,990
$16,990
CarGurus Analysis:
2020 Jeep Cherokee
With 51 currently listed for sale and an average price of $15,813 CAD, 15.7% of 2020 Jeep Cherokee listings on CarGurus are rated as good or great deals.
Favourably reviewed: Owners rated the 2020 Jeep Cherokee 4.77 / 5 stars.
- Year:
- 2021
- Make:
- Jeep
- Model:
- Cherokee
- Body type:
- SUV / Crossover
- Transmission:
- Automatic
- Mileage:
- 129,198
- Stock #:
- 9281
- VIN:
- 1C4PJMCB5MD200628
2021 Jeep Cherokee
North 4WD
129,198 km
$19,995
- Year:
- 2020
- Make:
- Jeep
- Model:
- Cherokee
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 271 hp 3.2L V6
- Exterior colour:
- Gray
- Combined gas mileage:
- 12 L/100km
- Fuel type:
- Gasoline
- Interior colour:
- Black
- Transmission:
- Automatic
- Mileage:
- 66,289
- Stock #:
- A-8788
- VIN:
- 1C4PJMBX5LD500276
2020 Jeep Cherokee
Trailhawk 4WD
66,289 km
$23,290
- Year:
- 2021
- Make:
- Jeep
- Model:
- Cherokee
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 271 hp 3.2L V6
- Combined gas mileage:
- 11 L/100km
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 81,178
- Stock #:
- K52426
- VIN:
- 1C4PJMDX4MD145874
2021 Jeep Cherokee
Limited 4WD
81,178 km
$23,836
- Year:
- 2021
- Make:
- Jeep
- Model:
- Cherokee
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 271 hp 3.2L V6
- Exterior colour:
- Red
- Combined gas mileage:
- 11 L/100km
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 99,079
- Stock #:
- 39786A
- VIN:
- 1C4PJMDX3MD106631
-$772
2021 Jeep Cherokee
Limited 4WD
99,079 km
$24,768
$24,718
- Year:
- 2021
- Make:
- Jeep
- Model:
- Cherokee
- Body type:
- SUV / Crossover
- Exterior colour:
- Orange
- Transmission:
- Automatic
- Mileage:
- 37,955
- Stock #:
- 262371
- VIN:
- 1C4PJMCX0MD228476
2021 Jeep Cherokee
North 4WD
37,955 km
$25,995
- Year:
- 2020
- Make:
- Jeep
- Model:
- Cherokee
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 271 hp 3.2L V6
- Exterior colour:
- Gray (Dark Grey)
- Combined gas mileage:
- 12 L/100km
- Fuel type:
- Gasoline
- Interior colour:
- Black
- Transmission:
- 9-Speed Automatic
- Mileage:
- 60,200
- Stock #:
- N9218
- VIN:
- 1C4PJMBX4LD529218
-$1,000
2020 Jeep Cherokee
Trailhawk 4WD
60,200 km
$22,777
$22,600
- Year:
- 2021
- Make:
- Jeep
- Model:
- Cherokee
- Body type:
- SUV / Crossover
- Exterior colour:
- Black
- Transmission:
- Automatic
- Mileage:
- 69,349
- Stock #:
- U12811A
- VIN:
- 1C4PJMBX7MD184901
2021 Jeep Cherokee
Trailhawk Elite 4WD
69,349 km
$24,158
- Year:
- 2021
- Make:
- Jeep
- Model:
- Cherokee
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 271 hp 3.2L V6
- Exterior colour:
- Silver
- Combined gas mileage:
- 12 L/100km
- Fuel type:
- Gasoline
- Interior colour:
- Black
- Transmission:
- Automatic
- Mileage:
- 117,000
- Stock #:
- 26T798A
- VIN:
- 1C4PJMBX9MD197813
2021 Jeep Cherokee
Trailhawk 4WD
117,000 km
$23,375
- Year:
- 2021
- Make:
- Jeep
- Model:
- Cherokee
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 180 hp 2.4L I4
- Exterior colour:
- Diamond Black Crystal Pearl
- Combined gas mileage:
- 10 L/100km
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 24,988
- Stock #:
- E3241
- VIN:
- 1C4PJMMN7MD149268
2021 Jeep Cherokee
Altitude 4WD
24,988 km
$29,159
- Year:
- 2019
- Make:
- Jeep
- Model:
- Cherokee
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 271 hp 3.2L V6
- Exterior colour:
- Red
- Combined gas mileage:
- 12 L/100km
- Fuel type:
- Gasoline
- Interior colour:
- Black
- Transmission:
- Automatic
- Mileage:
- 77,249
- Stock #:
- 260200B
- VIN:
- 1C4PJMBX6KD196700
Sponsored Listing
2019 Jeep Cherokee
Trailhawk 4WD
77,249 km
$22,199
CarGurus Analysis: 2020 Jeep Cherokee
Summary
With 51 currently listed for sale and an average price of $15,813 CAD, 15.7% of 2020 Jeep Cherokee listings on CarGurus are rated as good or great deals.
Favourably reviewed: Owners rated the 2020 Jeep Cherokee 4.77 / 5 stars.
Why it stands out
The 2020 Jeep Cherokee stands out as a compact SUV that blends Jeep styling with everyday usability. By this point in the third-generation Cherokee’s run, it had already moved away from the brand’s older, more rugged formula and into a softer crossover shape, but it still offered the kind of all-weather traction and adventure appeal that helped make the nameplate popular with buyers who did not want a noisy, square, gas-guzzling SUV. For 2020, Jeep also added new wheels and colours across various trims, including Sangria and Spitfire Orange, and Alexa was added to Uconnect 8.4 systems with navigation.
It also remained notable for the range of equipment it could offer. The 2020 Cherokee had a 7-inch touchscreen as standard, along with Apple CarPlay and Android Auto, and the interior featured lighter colours on the lower trim panels, new cloth fabrics, gloss-black trim, and a revised centre console with a larger pocket for phones. Cargo space increased to 764 litres, which adds to its practicality. At the same time, this generation was not without drawbacks: the buying guide notes major transmission issues in early third-generation models, and its pros and cons section points to poor efficiency and some bad engines through the years.
Other model years to consider
- 2018 Jeep Cherokee
- Average price: $12,234 CAD
- Good/great deal percentage: 18.4%
- User rating: 4.8 / 5
- Total listings: 38
- 2019 Jeep Cherokee
- Average price: $13,770 CAD
- Good/great deal percentage: 15.4%
- User rating: 4.67 / 5
- Total listings: 39
- 2026 Jeep Cherokee
- Average price: $48,629 CAD
- Good/great deal percentage: 39.1%
- Total listings: 23
Similar models to consider
- 2020 Ford Escape
- Average price: $14,239 CAD
- Good/great deal percentage: 15.1%
- User rating: 4.42 / 5
- Total listings: 73
- 2020 Nissan Rogue
- Average price: $14,462 CAD
- Good/great deal percentage: 12.9%
- User rating: 4.67 / 5
- Total listings: 70
This analysis is based on CarGurus' proprietary market data from October 5, 2026, CarGurus experts' opinions, and generative AI.
4.8 Overall rating
Filter by rating
Amanda W
Reviewed a 2020 Jeep Cherokee on May 5, 2025
This is a great vehicle. It has every feature that I asked for & more. It will have no issue towing my camper or hauling my kayaks.
Steinar A
Reviewed a 2020 Jeep Cherokee on Mar 10, 2023
I am.... impressed with the 2020 Jeep Cherokee Trailhawk. Specifically, the non-elite version has less fluff and is less likely to need repair amongst the electronics (no panorama roof, no rear tailgate motor, no advanced controls such as advanced cruise control, no heated seats or heated steering wheel & no NAV - etc. It does what it is supposed to do. I am also averaging 28 mpg versus the listed 24 mpg. I also added Falken Wildpeak ATW/3 tires to it (which makes it a better off road vehicle) also. Im pleased as punch with this Cherokee. Its a shame that Stellantis (Chrysler/Jeeps parent company) did not support this line of vehicles for the past 2 years & shut down the Belvidere plant (20 miles away from me) last month. There is zero reason why Stellantis cannot make money on this line of vehicles.
Michael W
Reviewed a 2020 Jeep Trailhawk Elite 4WD on Jul 29, 2024
The vehicle is very capable on and off road. Plenty of power to get up to speed on the highway, pass someone, and 4500lb towing capacity. Also it is the only trailhawk in the lineup to have a true rear locker.
Douglas B
Reviewed a 2020 Jeep Cherokee on Jun 28, 2022
The only thing I dont like about the 2020 jeep Cherokee is the power. It lacks the take off power I prefer. But other than that its a beautiful vehicle rides smoothly and is comfortable.
2020 Jeep Cherokee Trims
| Trim type | MSRP |
|---|---|
| Upland 4WD | $30,720 |
| Overland 4WD | $38,495 |
| Altitude FWD | $28,790 |
| Sport 4WD | -- |
| North 4WD | $31,800 |
| Limited 4WD | $34,845 |
| Trailhawk Elite 4WD | $37,950 |
| Trailhawk 4WD | $34,755 |
2020 Jeep Cherokee Price Trends
CarGurus tracks the prices of millions of used car listings every year. See how the average price of 2020 Jeep Cherokee prices has changed over time.
See more price trends2020 Jeep Cherokee Pricing Analysis: Windsor, ON Market Report
Pricing in Nearby Cities
Market Area: Windsor, ON
Key Insights
- Highest-Price Market: The London, ON market shows the highest average price at $24,500 CAD, indicating a premium demand in that area.
- Best Value: The Sarnia, ON market offers the lowest average price at $15,960 CAD, presenting a significant opportunity for budget-conscious shoppers.
- Inventory Drives Stability: The Cambridge, ON area leads with 132 listings, suggesting a robust supply that may help stabilise prices.
City-Level Pricing
| City | Total Listings | Avg Price |
|---|---|---|
| Cambridge, ON | 132 | $19,301 CAD |
| Guelph, ON | 131 | $19,301 CAD |
| Brantford, ON | 116 | $19,283 CAD |
| Kitchener, ON | 115 | $19,283 CAD |
| Cayuga, ON | 111 | $19,253 CAD |
| Selkirk, ON | 91 | $19,006 CAD |
| Listowel, ON | 84 | $22,498 CAD |
| Woodstock, ON | 82 | $21,080 CAD |
| London, ON | 75 | $24,500 CAD |
| Sarnia, ON | 62 | $15,960 CAD |
Pricing by Trim Packages
Key Insights
- Volume Leader: The Trailhawk 4WD trim is the most popular with 39 listings, indicating strong consumer preference for this configuration.
- Premium Spread: The Overland 4WD trim, priced at $38,495 CAD, represents the highest MSRP, highlighting a significant premium for luxury features.
- Drivetrain Effect: All trims are equipped with 4X4 drivetrains, which may appeal to buyers seeking enhanced capability in various driving conditions.
Trim-Level Details
| Trim | Listings | MSRP | Drivetrain | Engine |
|---|---|---|---|---|
| Trailhawk 4WD | 39 | $34,755 CAD | 4X4 | 3.2L 271 hp V6 |
| Limited 4WD | 22 | $34,845 CAD | 4X4 | 3.2L 271 hp V6 |
| North 4WD | 21 | $31,800 CAD | 4X4 | 3.2L 271 hp V6 |
| Altitude 4WD | 12 | $30,290 CAD | 4X4 | 2.4L 180 hp I4 |
| Trailhawk Elite 4WD | 12 | $37,950 CAD | 4X4 | 3.2L 271 hp V6 |
| Overland 4WD | 6 | $38,495 CAD | 4X4 | 3.2L 271 hp V6 |
Pricing Analysis by Model Year
Key Insights
- New-Car Premium: The 2026 model year commands an average price of $48,629 CAD, reflecting a 38.9% premium over its starting MSRP, indicating strong demand for newer models.
- Depreciation Curve: The 2014 model year exhibits the steepest depreciation at -65.5%, suggesting significant value loss over time for older models.
- Best Value Sweet Spot: The 2020 model year, priced at an average of $15,757 CAD, represents a compelling value for buyers looking for a balance between cost and features.
Model Year Pricing
| Model Year | Starting MSRP | Avg Price | Avg Price vs Starting MSRP |
|---|---|---|---|
| 2026 | $35,000 CAD | $48,629 CAD | +38.9% |
| 2023 | $37,695 CAD | $27,807 CAD | -26.2% |
| 2022 | $29,995 CAD | $22,003 CAD | -26.6% |
| 2021 | $27,890 CAD | $18,348 CAD | -34.2% |
| 2020 | $25,840 CAD | $15,757 CAD | -39.0% |
| 2019 | $25,045 CAD | $13,712 CAD | -45.3% |
| 2018 | $24,395 CAD | $12,228 CAD | -49.9% |
| 2017 | $23,695 CAD | $11,340 CAD | -52.1% |
| 2016 | $23,495 CAD | $9,966 CAD | -57.6% |
| 2015 | $23,095 CAD | $8,441 CAD | -63.5% |
| 2014 | $22,995 CAD | $7,924 CAD | -65.5% |
These recommendations are based on CarGurus' proprietary market data from October 6, 2026, CarGurus experts' opinions, and generative AI.
How much does the 2020 Jeep Cherokee cost?
| Metric | Value |
|---|---|
| Current Average Price | $21,249 CAD |
| Year-Round Low | $21,249 CAD |
| Year-Round High | $25,284 CAD |
| Average Price a Year Ago | $25,284 CAD |
| Change vs. Last Year | −15.96% |
Prices have softened 15.96% compared to this time last year, making it a favourable time to shop this model year.
There are 499 listings available, which suggests a healthy amount of inventory for you to compare.
Is the 2020 Jeep Cherokee a good car?
Yes — the 2020 Jeep Cherokee earns a 4.77/5 user rating, which points to strong owner satisfaction. Drivers commonly praise its strong performance, comfortable ride, and spacious, well-equipped interior. It also fits well if you want a compact SUV with everyday usability and Jeep-style all-weather traction, while the market still shows 27.3% of listings as good or great deals.
Is the 2020 Jeep Cherokee reliable?
Owners rate it 4.77/5, a strong signal of long-term satisfaction.
The user feedback points to a vehicle that many owners find dependable in daily use, with praise for its comfortable ride and strong performance. That said, some drivers mention concerns with certain features and acceleration, so a careful test drive still matters. For used buyers, the main long-term ownership risk is making sure the specific vehicle has been maintained well and feels solid in real-world driving.
Is now a good time to buy a used 2020 Jeep Cherokee?
This looks like a moderate, selective buyer’s market, so you have room to shop carefully rather than rush.
- Deal availability: 27.3% of listings are priced as good or great deals.
- Inventory: There are 499 listings available.
- Price trend: Prices have softened 15.96% compared with last year.
If you find a listing below $21,249 CAD, that's toward the low end of the year-round range and worth acting on quickly.
What is the 2020 Jeep Cherokee's resale value?
The current average of $21,249 CAD sits slightly below last year's $25,284 CAD.
That price movement suggests the market has cooled, which can make the Cherokee easier to buy now but may also limit upside for a future seller if prices stay soft. If you plan to resell later, the current trend means you should focus on buying well and keeping the vehicle in strong condition. Vehicles with strong owner satisfaction ratings, like this model year's 4.77/5, tend to retain buyer demand, which supports resale value over time.
Should I buy a 2020 Jeep Cherokee or consider a different year?
If you're weighing the 2020 against nearby model years, here's how to think about it:
Choose the 2020 if:
- 27.3% of listings are priced as good or great deals.
- Price trend: Prices have softened 15.96% compared with last year.
- Owners rate it 4.77/5 — a strong satisfaction signal.
The bottom line: The 2020 Cherokee makes sense if you want a used compact SUV with strong owner approval, a softer price trend, and enough inventory to compare options. If you are especially price-sensitive, you may also want to look at nearby model years and compare the specific listings that fall into the best-deal range before deciding.
These recommendations are based on CarGurus' proprietary market data from October 6, 2026, CarGurus experts' opinions, and generative AI.
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