Best Seller
Urban Outfitters Shoes | Black Urban Outfitters Chelsea Ankle Boots. Size 8. Fair Condition. | Color: Black | Size: 8

Urban Outfitters Shoes | Black Urban Outfitters Chelsea Ankle Boots. Size 8. Fair Condition. | Color: Black | Size: 8

Black Urban Outfitters Ankle Boots In Size 8. Fit True To Size. These Are In Fair Condition With Some Scuffs, Peeling (Especially On Right Boot), And Bending From Wear. The Heels And Bottoms Are In Great Condition. Please Zoom Into Pictures And Reach... more

$9.00

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Madewell Shoes | Madewell Sonia Chelsea Ankle Bootie Boot Snakeskin 6 | Color: Brown | Size: 6

Madewell Shoes | Madewell Sonia Chelsea Ankle Bootie Boot Snakeskin 6 | Color: Brown | Size: 6

Madewell Sonia Chelsea Boot Color: Brown Snakeskin Size 6 Style #M3463 Retail $188 New W/O Box An Almond Toe And Tapered, Stacked Heel Bring A Contemporary Look To A Chelsea Boot That Serves As A Versatile Work-To-Weekend Style. Pull-On Style With... more

$50.00

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Best Seller
Free People Shoes | Free People James Black Leather Chelsea Heeled Ankle Boot Nwot | Color: Black | Size: 11

Free People Shoes | Free People James Black Leather Chelsea Heeled Ankle Boot Nwot | Color: Black | Size: 11

Free People James Black Leather Chelsea Heeled Ankle Boot Nwot Sz 41 Make Me An Offer! Special Discounts Available For Bundles Of 2 Items Or More! Questions? Leave A Comment Below! more

$125.00

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Coach Shoes | Coach Mens Chelsea Boots Ankle Suede Pull-On Round Toe Leather Insole Brown 8.5d | Color: Brown | Size: 8.5

Coach Shoes | Coach Mens Chelsea Boots Ankle Suede Pull-On Round Toe Leather Insole Brown 8.5d | Color: Brown | Size: 8.5

Coach Mens Chelsea Boots Ankle Suede Pull-On Round Toe Leather Insole Brown 8.5d Pull On Round Toe Features A Comfortable Crepe Sole Ribbed Ankle Gores Pull Tab For On-And-Off Ease. Style No. G2290 Suede Upper Leather Lining And Footbed Rubber Outsole... more

$69.00

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Madewell Shoes | Madewell Bryce Ankle Boot Suede Chelsea Chestnut Tan Heeled Size 7 | Color: Brown/Tan | Size: 7

Madewell Shoes | Madewell Bryce Ankle Boot Suede Chelsea Chestnut Tan Heeled Size 7 | Color: Brown/Tan | Size: 7

Pre-Owned, Good Gently Used Condition Some Marks Madewell Bryce Suede Boots Heeled Ankle Boots Chelsea Camel Brown Chestnut Tan Size 7 Genuine Suede 2.5" Heel Offers Always Welcome Bundle Items To Save! Sorry No Trades Or Holds more

$53.00

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Free People Shoes | Free People Atlas Suede Chelsea Ankle Boot Sz 36/Us 6 | Color: Brown | Size: 6

Free People Shoes | Free People Atlas Suede Chelsea Ankle Boot Sz 36/Us 6 | Color: Brown | Size: 6

Free People Atlas Suede Chelsea Ankle Boot Sz 36/Us 6 Pieced Leopard Printed Leather Pull-On Bootie Elasticized Insets Scalloped Trim And Stud Details Cushioned Footbed 5 1/2" Shaft Leather Upper/Lining. Manmade Outsole. New Without Box, Never Worn,... more

$134.00

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Anthropologie Shoes | Anthropologie ~Stompy Chelsea Ankle Pull On Brown Leather Boots ~ 39/Us 7.5-8 | Color: Brown | Size: 8

Anthropologie Shoes | Anthropologie ~Stompy Chelsea Ankle Pull On Brown Leather Boots ~ 39/Us 7.5-8 | Color: Brown | Size: 8

In Good Shape Size 39 more

$60.00

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J. Crew Shoes | Black Chelsea Ankle Boots 6.5 | Color: Black | Size: 6.5

J. Crew Shoes | Black Chelsea Ankle Boots 6.5 | Color: Black | Size: 6.5

These Are Black Chelsea Ankle Boots That I Wore So Religiously That I Bought Two Pairs When They Were On Sale As Back Up. I Don’t Need Two Extra Pairs Tho So I’m Selling These Now. Have Hardly Been Worn But Were In Storage For A While And They Deserve... more

$60.00

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Madewell Shoes | Madewell The Grayson Brogue Chelsea Bootie Western Cut Suede Ankle Boots | Color: White | Size: 7

Madewell Shoes | Madewell The Grayson Brogue Chelsea Bootie Western Cut Suede Ankle Boots | Color: White | Size: 7

Size 8 In Good Condition And I Didn't Find Any Flaws more

$60.00

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Free People Shoes | Free People Castillo Chelsea Boots Ankle Size 38 | Color: Brown/Red | Size: 8

Free People Shoes | Free People Castillo Chelsea Boots Ankle Size 38 | Color: Brown/Red | Size: 8

Free People Castillo Chelsea Boot - Size 38 Eu/ Us Women’s 8. Fits Size 8.5 Snug. Purchased From Free People Directly Years Ago And Held Onto Them Because They’re So Cute But Unfortunately A Little Too Small For Me. Made With Real Patent Leather And... more

$40.00

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Michael Kors Shoes | Michael Kors Light Tan Suede Leather Stacked Heel Chelsea Ankle Boots Size 8.5 | Color: Brown/Tan | Size: 8.5

Michael Kors Shoes | Michael Kors Light Tan Suede Leather Stacked Heel Chelsea Ankle Boots Size 8.5 | Color: Brown/Tan | Size: 8.5

Michael Kors Booties 3.5" Heels 5" Shaft These Do Have Some Significant Wear On The Heels, Still A Lot Of Life Left! Please See Photos. Women's Size 8.5 @Boyds_boutique A# more

$36.00

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Free People Shoes | Heiress X Free People Caleb Chelsea Gold Metallic Ankle Boot - Size 7 | Color: Black/Gold | Size: 7

Free People Shoes | Heiress X Free People Caleb Chelsea Gold Metallic Ankle Boot - Size 7 | Color: Black/Gold | Size: 7

In Good Condition, See Last Pictures For Some Slight Scratches (Not Visible While Wearing!) Textured Rubber Heel. Pull Tab In Back For An Easy On/Off. Padded Footbed. more

$50.00

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Madewell Shoes | Madewell Sz 7 The Regan Chelsea Ankle Boots Black Leather Stacked Block Heel | Color: Black | Size: 7

Madewell Shoes | Madewell Sz 7 The Regan Chelsea Ankle Boots Black Leather Stacked Block Heel | Color: Black | Size: 7

Step Up Your Shoe Game With These Stylish Chelsea Ankle Boots By Madewell. Crafted With Black Leather, These Boots Feature A Round Toe Shape And A Pull-On Closure For Easy Wear. The Mid-Height Stacked Block Heel Provides Comfort And Style, Making Them... more

$76.00

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Free People Shoes | Free People Brooks Lug Sole Chelsea Boot Tall Ankle Leather Shoes Black Suede | Color: Black | Size: 8

Free People Shoes | Free People Brooks Lug Sole Chelsea Boot Tall Ankle Leather Shoes Black Suede | Color: Black | Size: 8

Free People Brooks Lug Sole Chelsea Boot Tall Ankle Leather Shoes Black Suede Size 38/Us 8 Nwob New Without Box. Store Display Model. Minor Wear From Being Tried On In A Retail Environment. Please See Photos. Never Worn Outside. Smoke Free Home. Fast... more

$90.00

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Zara Shoes | Men Zara Casual Beige Leather Ankle Chelsea Boots | Color: Cream/Tan | Size: 10

Zara Shoes | Men Zara Casual Beige Leather Ankle Chelsea Boots | Color: Cream/Tan | Size: 10

Negotiable ! Brand New With Tags Attached Never Worn *Please Note Tag Doesn’t Include Price Size 10 Not In The Box ! Original Price $149.90 more

$150.00

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Coach Shoes | Coach Chelsea Leather Ankle Boot | Color: Green | Size: 10

Coach Shoes | Coach Chelsea Leather Ankle Boot | Color: Green | Size: 10

Leather Upper Man-Made Leather Lining And Footbed Leather Outsole Pull On Side Gore In Darker Green Nwot. Box Not Included. Smells Of Leather. No Flaws. Fast Shipping. more

$118.00

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Madewell Shoes | - Madewell Chelsea Tan Slip On Ankle Boots Sz 9 | Color: Tan | Size: 9

Madewell Shoes | - Madewell Chelsea Tan Slip On Ankle Boots Sz 9 | Color: Tan | Size: 9

Tan Leather With Elastic Stretch On Both Side For Easy Slip On Round Toe Leather Sole Preowned But In Good Condition more

$65.00

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Free People Shoes | Free People Beau Western Chelsea Ankle Pointed Boots Gold Size Eu 37 / Us 7 | Color: Gold | Size: 7

Free People Shoes | Free People Beau Western Chelsea Ankle Pointed Boots Gold Size Eu 37 / Us 7 | Color: Gold | Size: 7

Free People Beau Western Chelsea Ankle Pointed Boots Gold Size Eu 37 / Us 7 Brand : Free People Style : Beau Western Chelsea Boot Color : Gold Size 37 Us 7 Sku No : 8573 Condition : New Without Box more

$115.00

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Kate Spade Shoes | Kate Spade New York Star Sedgewick Rubber Chelsea Ankle Boots Size 11 Rain New | Color: Black | Size: 11

Kate Spade Shoes | Kate Spade New York Star Sedgewick Rubber Chelsea Ankle Boots Size 11 Rain New | Color: Black | Size: 11

Kate Spade New York Star Sedgewick Rubber Chelsea Ankle Boots Size 11 Rain New New In Box Condition Notes: Display Or Try On Boot - No Dust Bag Or Box When It Rains, You'll Shine In Kate Spade New York's Star Chelsea-Style Boots With Gleaming Gold-Tone... more

$105.00

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J. Crew Shoes | J Crew Cognac Brown Chelsea Pull On Boots Ankle Booties Size 8 Eo824 | Color: Brown | Size: 8

J. Crew Shoes | J Crew Cognac Brown Chelsea Pull On Boots Ankle Booties Size 8 Eo824 | Color: Brown | Size: 8

J Crew Cognac Brown Leather Chelsea Boots With Stretch Panels For Easy Pull-On. Tag Size 8. Fits 7.5-8 In My Opinion. Style Eo824 Preowned. Shows Signs Of Wear Including Scuffs On Toes, Wear On Back Heels, Wear On Bottoms Of Soles, Creasing In Midfoot... more

$50.00

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J. Crew Shoes | J.Crew Sherpa Lined Suede Chelsea Ankle Boots 7.5 | Color: Tan | Size: 7.5

J. Crew Shoes | J.Crew Sherpa Lined Suede Chelsea Ankle Boots 7.5 | Color: Tan | Size: 7.5

New Without Box Size 7.5 more

$90.00

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Madewell Shoes | Madewell Regan Taupe Suede Leather Stacked Heel Ankle Chelsea Boots Sz 9.5 | Color: Gray/Tan | Size: 9.5

Madewell Shoes | Madewell Regan Taupe Suede Leather Stacked Heel Ankle Chelsea Boots Sz 9.5 | Color: Gray/Tan | Size: 9.5

Taupe Suede Heeled Chelsea Boots From Madewell. Worn Only A Couple Times And Still In Excellent Condition. Very Cute And Great For Fall! Size 9.5 Please Let Me Know If You Have Any Questions Or Would Like Additional Photos. more

$75.00

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Madewell Shoes | Madewell Sonia Black Leather Chelsea Ankle Boot Slightly Used | Color: Black | Size: 9

Madewell Shoes | Madewell Sonia Black Leather Chelsea Ankle Boot Slightly Used | Color: Black | Size: 9

Questions? Leave A Comment Below! more

$35.00

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Free People Shoes | Free People Beau Western Boot Eu 36 Us 6 Gold Ankle Chelsea Bootie Croc Pointed | Color: Gold | Size: 36eu

Free People Shoes | Free People Beau Western Boot Eu 36 Us 6 Gold Ankle Chelsea Bootie Croc Pointed | Color: Gold | Size: 36eu

Free People Beau Western Boot In Gold Size 36 (Equivalent To A Us Women's Size 6 Per Free People Website) Slip-On Western-Style Chelsea Boot Silhouette Ankle-Height Shaft Lightly-Distressed Metallic Gold Croc Embossed Leather Upper Pointed Snip Toe... more

$53.00

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Madewell Shoes | Madewell The Grayson Brogue Chelsea Boot Suede Ankle Booties Western Oxford 8 | Color: Brown | Size: 8

Madewell Shoes | Madewell The Grayson Brogue Chelsea Boot Suede Ankle Booties Western Oxford 8 | Color: Brown | Size: 8

Madewell The Grayson Brogue Chelsea Boot. Saddle Brown Suede Leather Ankle Booties. Rustic Footwear With Western Kick. Wingtip Oxford Detailing, Stretch Side Gussets, Back Pull Tab To Help With Slide On / Slip On Styling. Cushioned Insoles, Leather... more

$79.00

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Kate Spade Shoes | Kate Spade Brandi Tan Natural Desert Leather Chelsea Ankle Boots Sz 6.5 | Color: Tan | Size: 6.5

Kate Spade Shoes | Kate Spade Brandi Tan Natural Desert Leather Chelsea Ankle Boots Sz 6.5 | Color: Tan | Size: 6.5

Kate Spade Brandi Tan Natural Desert Leather Chelsea Ankle Boots Sz 6.5 Kate Spade New York Brandi Tan Pebbled Leather Ankle Boots With Bow Pointed Toe- Solid Vamp- Buckle Strap Detail- Bow Tie Embellishment- Shaft Height, 10." Opening Circumference-... more

$48.00

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Madewell Shoes | New Madewell Sonia Snake Embossed Chelsea Block Heel Ankle Boots Size 7.5 | Color: Black/Tan | Size: 7.5

Madewell Shoes | New Madewell Sonia Snake Embossed Chelsea Block Heel Ankle Boots Size 7.5 | Color: Black/Tan | Size: 7.5

New Madewell Sonia Snake Embossed Low Chelsea Block Heel Ankle Boots Size 7.5 - Almond Toe Tapered, Stacked Heel - Chelsea Boot - 1 3/4" Heel, 3" Shaft - Pull-On Style - Elastic Gore Insets - Cushioned Footbed - Leather Upper And Lining/Synthetic Sole... more

$99.00

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Madewell Shoes | Madewell Sonia Chelsea Ankle Bootie Boot Leather Snakeskin 11 M3463 | Color: Black/Brown | Size: 11

Madewell Shoes | Madewell Sonia Chelsea Ankle Bootie Boot Leather Snakeskin 11 M3463 | Color: Black/Brown | Size: 11

Good Preowned Condition. Light Wear As Shown In Photos. An Almond Toe And Tapered, Stacked Heel Bring A Contemporary Look To A Chelsea Boot That Serves As A Versatile Work-To-Weekend Style. Pull-On Style With Elastic Gore Insets Cushioned Footbed... more

$68.00

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Free People Shoes | Free People Beau Western Ankle Chelsea Boot Embossed Gold Leather | Color: Black/Gold | Size: Various

Free People Shoes | Free People Beau Western Ankle Chelsea Boot Embossed Gold Leather | Color: Black/Gold | Size: Various

New Without Box (Has Tags) Multiple Sizes Available Free People Beau Western Ankle Chelsea Boot Embossed Gold Leather Embossed Reptile Genuine Leather Chelsea Western Style Gold Metallic Block Heel 1.5" Pointed Toe Made In India. Elastic Side Gussets.... more

$178.00

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Gucci Shoes | Gucci Cordovan Lux Pointed Toe Side Buckle Chelsea Ankle Boots White Size 37 New | Color: White | Size: 37eu

Gucci Shoes | Gucci Cordovan Lux Pointed Toe Side Buckle Chelsea Ankle Boots White Size 37 New | Color: White | Size: 37eu

Gucci Cordovan Lux Pointed Toe Side Buckle Chelsea Ankle Boots Great White Size 37 New With Dustbags, No Box, Very Minor Signs Of Retail Environment Try Ons As Photographed, Size 37, Per Brand Equivalent To Us Size 7, Authenticity Guaranteed. All... more

$515.00

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Madewell Shoes | Madewell Spencer Taupe Chelsea Slip On Leather Ankle Boots Size 8.5 | Color: Tan | Size: 8.5

Madewell Shoes | Madewell Spencer Taupe Chelsea Slip On Leather Ankle Boots Size 8.5 | Color: Tan | Size: 8.5

Madewell Spencer Taupe Chelsea Slip On Leather Ankle Boots Slip On Stacked Block Heel Chelsea Style Ankle Length Western Leather Upper And Lining Taupe Color Size: 8.5 Condition: Good, Has Some Scuffing more

$50.00

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Free People Shoes | Free People Western Ankle Leather Chelsea Boots Size 7.5=8.5 Retail $178 | Color: Black | Size: 7.5

Free People Shoes | Free People Western Ankle Leather Chelsea Boots Size 7.5=8.5 Retail $178 | Color: Black | Size: 7.5

Bran New In A Box. Size 7.5 But They Run 1 Size Bigger =8.5. Genuine Embossed Croc Leather. Black Elastic Sides, Pointy Toe. Curved Hills 1.75” more

$75.00

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Gucci Shoes | Gucci Boots Mens Chelsea Ankle Black Leather Logo Hardware Sz 11 11.5 | Color: Black | Size: 11.5

Gucci Shoes | Gucci Boots Mens Chelsea Ankle Black Leather Logo Hardware Sz 11 11.5 | Color: Black | Size: 11.5

Designer: Gucci Size: Marked As 11 / Us 11.5 (Conversion Per Designer's Website) Condition: Authentic And Brand New Style Name / Number: 624661 Cdzk0 1000 Material: Leather Upper, Leather Unique Features: Classic Black Leather Mens Chelsea Ankle Boots.... more

$599.00

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Free People Shoes | Free People James Chelsea Black Boots Chunky Feels Ankle Booties 38.5 Us 8 | Color: Black/Cream | Size: 8

Free People Shoes | Free People James Chelsea Black Boots Chunky Feels Ankle Booties 38.5 Us 8 | Color: Black/Cream | Size: 8

New With Box Size 38.5 / Us 8.5 Make A Statement In These So Cool Leather Chelsea Boots Featured In A Chunky Heeled Design With Elastic Side Details And A Slim Silhouette. These Boots Feature Intentionally Distressed Detailing For A Worn-In Look. Side... more

$170.00

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Free People Shoes | Free People Arlo Santa Fe Ankle Chelsea Boots Black Crocodile Snake Size 7 | Color: Black | Size: 7

Free People Shoes | Free People Arlo Santa Fe Ankle Chelsea Boots Black Crocodile Snake Size 7 | Color: Black | Size: 7

Free People Arlo Santa Fe Ankle Boots Size: European 37.5 (Us 7) Color: Black Crocodile Basically Brand New. Sales Sticker Still On Sole. Only Worn Once. Condition: These Shoes Are Intentionally Distressed. Brand New, They Intentionally Look Worn In,... more

$80.00

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Free People Shoes | Free People Vegan Chelsea Gray Ankle Boots | Color: Gray | Size: 8

Free People Shoes | Free People Vegan Chelsea Gray Ankle Boots | Color: Gray | Size: 8

Size 8 Block Heel In Good Condition more

$60.00

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American Eagle Outfitters Shoes | Brown Chelsea Ankle Boots | Color: Brown | Size: 6

American Eagle Outfitters Shoes | Brown Chelsea Ankle Boots | Color: Brown | Size: 6

Brown Chelsea Booties Size 6 From American Eagle Tiny Signs Of Wear On The Heels But Good Condition Still!! more

$18.00

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Madewell Shoes | Madewell Suede Chelsea Ankle Boots | Color: Brown | Size: 9.5

Madewell Shoes | Madewell Suede Chelsea Ankle Boots | Color: Brown | Size: 9.5

New Without A Box Madewell Suede Chelsea Ankle Boots In Size 9.5 Medium.There’s A Small Black Line As Shown On Photo more

$130.00

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J. Crew Shoes | J Crew Chelsea Boot Ankle Brown Size 10 | Color: Brown | Size: 10

J. Crew Shoes | J Crew Chelsea Boot Ankle Brown Size 10 | Color: Brown | Size: 10

J Crew Chelsea Brown Leather Booties Size 10. It Is Comfortable. Soft Leather Pet/Smoke Free Home. Please See Pictures For More Details. more

$58.00

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J. Crew Shoes | Black Madewell Chunky Chelsea Ankle Boot. Size 8.5. | Color: Black | Size: 8.5

J. Crew Shoes | Black Madewell Chunky Chelsea Ankle Boot. Size 8.5. | Color: Black | Size: 8.5

Black Madewell Chunky Chelsea Ankle Boot. Size 8.5. Never Worn. New In Box. more

$150.00

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