United States Software & IT Services

Guidewire Software Inc (GWRE)

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Over the last 90 days, Guidewire Software Inc. has seen significant insider selling, with a net value of -$2.38 million. Executives have been net sellers, contributing to a negative net insider count. Notable transactions include multiple planned and proposed sales by CEO Michael George Rosenbaum and Officer/Director Mike Rosenbaum, totaling over $1.6 million in recent weeks.
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Ticker: GWRE Exchange: NYS
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• Purchase • Sale • Planned purchase • Planned sale Net purchase Net sale Activity signal Earnings
Top insiders
Trades
Rosenbaum Michael George
Chief Executive Officer
1 sale — total 100,000 USD
Planned sale 8 Jun 2026
Value US$4,416,218.99 | Price 487.98 | Shares 53,063
Proposed sale 8 Jun 2026
Value US$990,629.13 | Price 460.90 | Shares 42,581
Planned sale 1 Jun 2026
Value US$100,000.00 | Price 158.92 | Shares 1,000
Proposed sale 1 Jun 2026
Value US$100,000.00 | Price 158.92 | Shares 1,000
Planned sale 26 May 2026
Value US$100,000.00 | Price 138.51 | Shares 1,000
Proposed sale 26 May 2026
Value US$100,000.00 | Price 138.51 | Shares 1,000
Planned sale 18 May 2026
Value US$153,828.00 | Price 128.19 | Shares 1,200
Proposed sale 18 May 2026
Value US$153,828.00 | Price 128.19 | Shares 1,200
Planned sale 11 May 2026
Value US$163,656.00 | Price 136.38 | Shares 1,200
Proposed sale 11 May 2026
Value US$163,656.00 | Price 136.38 | Shares 1,200
Planned sale 4 May 2026
Value US$170,292.00 | Price 141.91 | Shares 1,200
Proposed sale 4 May 2026
Value US$170,292.00 | Price 141.91 | Shares 1,200
Planned sale 27 Apr 2026
Value US$165,708.00 | Price 138.09 | Shares 1,200
Proposed sale 27 Apr 2026
Value US$165,708.00 | Price 138.09 | Shares 1,200
Planned sale 20 Apr 2026
Value US$167,700.00 | Price 139.75 | Shares 1,200
Proposed sale 20 Apr 2026
Value US$167,700.00 | Price 139.75 | Shares 1,200
Planned sale 13 Apr 2026
Value US$142,524.00 | Price 118.77 | Shares 1,200
Proposed sale 13 Apr 2026
Value US$142,524.00 | Price 118.77 | Shares 1,200
Planned sale 6 Apr 2026
Value US$181,368.00 | Price 151.14 | Shares 1,200
Proposed sale 6 Apr 2026
Value US$181,368.00 | Price 151.14 | Shares 1,200
Planned sale 30 Mar 2026
Value US$174,888.00 | Price 145.74 | Shares 1,200
Proposed sale 30 Mar 2026
Value US$174,888.00 | Price 145.74 | Shares 1,200
Planned sale 23 Mar 2026
Value US$186,672.00 | Price 155.56 | Shares 1,200
Proposed sale 23 Mar 2026
Value US$186,672.00 | Price 155.56 | Shares 1,200
Sale 17 Mar 2026
Value US$44,733.21 | Price 163.86 | Shares 273
Sale 17 Mar 2026
Value US$164,021.76 | Price 163.86 | Shares 1,001
Sale 17 Mar 2026
Value US$317,065.04 | Price 163.86 | Shares 1,935
Sale 17 Mar 2026
Value US$1,077,529.55 | Price 163.86 | Shares 6,576
Sale 17 Mar 2026
Value US$776,194.87 | Price 163.86 | Shares 4,737
Proposed sale 17 Mar 2026
Value US$44,733.19 | Price 163.86 | Shares 273
Proposed sale 17 Mar 2026
Value US$164,021.72 | Price 163.86 | Shares 1,001
Proposed sale 17 Mar 2026
Value US$1,077,529.31 | Price 163.86 | Shares 6,576
Proposed sale 17 Mar 2026
Value US$317,064.96 | Price 163.86 | Shares 1,935
Proposed sale 17 Mar 2026
Value US$776,194.69 | Price 163.86 | Shares 4,737
Planned sale 16 Mar 2026
Value US$192,000.00 | Price 160.00 | Shares 1,200
Proposed sale 16 Mar 2026
Value US$192,000.00 | Price 160.00 | Shares 1,200
Proposed sale 13 Mar 2026
Value US$755,031.04 | Price 158.72 | Shares 4,757
Planned sale 13 Mar 2026
Value US$755,031.04 | Price 158.72 | Shares 4,757
Planned sale 9 Mar 2026
Value US$199,608.00 | Price 166.34 | Shares 1,200
Proposed sale 9 Mar 2026
Value US$199,608.00 | Price 166.34 | Shares 1,200
Planned sale 2 Mar 2026
Value US$172,644.00 | Price 143.87 | Shares 1,200
Proposed sale 2 Mar 2026
Value US$172,644.00 | Price 143.87 | Shares 1,200
Planned sale 23 Feb 2026
Value US$150,600.00 | Price 125.50 | Shares 1,200
Proposed sale 23 Feb 2026
Value US$150,600.00 | Price 125.50 | Shares 1,200
Planned sale 17 Feb 2026
Value US$152,400.00 | Price 127.00 | Shares 1,200
Proposed sale 17 Feb 2026
Value US$152,400.00 | Price 127.00 | Shares 1,200
Planned sale 9 Feb 2026
Value US$153,324.00 | Price 127.77 | Shares 1,200
Proposed sale 9 Feb 2026
Value US$153,324.00 | Price 127.77 | Shares 1,200
Proposed sale 4 Feb 2026
Value US$612,871.92 | Price 125.64 | Shares 4,878
Planned sale 2 Feb 2026
Value US$168,012.00 | Price 140.01 | Shares 1,200
Proposed sale 2 Feb 2026
Value US$168,012.00 | Price 140.01 | Shares 1,200
Proposed sale 26 Jan 2026
Value US$192,384.00 | Price 160.32 | Shares 1,200
Planned sale 26 Jan 2026
Value US$192,384.00 | Price 160.32 | Shares 1,200
Planned sale 20 Jan 2026
Value US$187,512.00 | Price 156.26 | Shares 1,200
Proposed sale 20 Jan 2026
Value US$187,512.00 | Price 156.26 | Shares 1,200
Planned sale 13 Jan 2026
Value US$39,067.92 | Price 180.87 | Shares 216
Planned sale 13 Jan 2026
Value US$217,044.00 | Price 180.87 | Shares 1,200
Proposed sale 13 Jan 2026
Value US$39,067.92 | Price 180.87 | Shares 216
Proposed sale 13 Jan 2026
Value US$217,044.00 | Price 180.87 | Shares 1,200
Proposed sale 29 Dec 2025
Value US$286,930.00 | Price 204.95 | Shares 1,400
Planned sale 29 Dec 2025
Value US$286,930.00 | Price 204.95 | Shares 1,400
Proposed sale 22 Dec 2025
Value US$281,008.00 | Price 200.72 | Shares 1,400
Planned sale 22 Dec 2025
Value US$281,008.00 | Price 200.72 | Shares 1,400
Proposed sale 18 Dec 2025
Value US$240,240.00 | Price 195.00 | Shares 1,232
Proposed sale 18 Dec 2025
Value US$362,700.00 | Price 195.00 | Shares 1,860
Planned sale 18 Dec 2025
Value US$240,240.00 | Price 195.00 | Shares 1,232
Planned sale 18 Dec 2025
Value US$362,700.00 | Price 195.00 | Shares 1,860
Sale 16 Dec 2025
Value US$551,642.56 | Price 192.08 | Shares 2,872
Sale 16 Dec 2025
Value US$279,854.88 | Price 192.08 | Shares 1,457
Sale 16 Dec 2025
Value US$1,155,337.74 | Price 192.08 | Shares 6,015
Sale 16 Dec 2025
Value US$68,763.24 | Price 192.08 | Shares 358
Sale 16 Dec 2025
Value US$1,531,806.90 | Price 192.08 | Shares 7,975
Proposed sale 16 Dec 2025
Value US$1,531,806.82 | Price 192.08 | Shares 7,975
Proposed sale 16 Dec 2025
Value US$551,642.53 | Price 192.08 | Shares 2,872
Proposed sale 16 Dec 2025
Value US$1,155,337.68 | Price 192.08 | Shares 6,015
Abbreviations B: Buy, S: Sell, PP: Planned purchase, PlS: Planned sale, PrS: Proposed sale, O: Option / Other
Notification date Transaction date B/S Transaction type Insider and/or position Nb. shares
Price
Value 		Number of shares Price Value Details
2026-06-08 2026-06-08 PlS Planned sale
3.3
Rosenbaum Michael George

Chief Executive Officer

Executive Director
53,063 +1.7%
487.98
US$4,416,219 		53,063 +1.7% 487.98 US$4,416,219
2026-06-08 2026-06-08 PrS Proposed sale
3.3
MIKE ROSENBAUM

Officer; Director

Executive Director
42,581
460.90
US$990,629 		42,581 460.90 US$990,629
2026-06-02 2026-06-01 PlS Planned sale
3.3
Rosenbaum Michael George

Chief Executive Officer

Executive Director
9,063 -18.9%
28.34
US$4,327,926 		9,063 -18.9% 28.34 US$4,327,926
2026-06-01 2026-06-01 PrS Proposed sale
3.3
MIKE ROSENBAUM

Officer; Director

Executive Director
1,000
158.92
US$100,000 		1,000 158.92 US$100,000
2026-05-26 2026-05-26 PlS Planned sale
3.3
Rosenbaum Michael George

Chief Executive Officer

Executive Director
1,000 -0.6%
138.51
US$100,000 		1,000 -0.6% 138.51 US$100,000
2026-05-26 2026-05-26 PrS Proposed sale
3.3
MIKE ROSENBAUM

Officer; Director

Executive Director
1,000
138.51
US$100,000 		1,000 138.51 US$100,000
2026-05-18 2026-05-18 PlS Planned sale
3.3
Rosenbaum Michael George

Chief Executive Officer

Executive Director
1,200 -0.6%
128.19
US$153,828 		1,200 -0.6% 128.19 US$153,828
2026-05-18 2026-05-18 PrS Proposed sale
3.3
MIKE ROSENBAUM

Officer; Director

Executive Director
1,200
128.19
US$153,828 		1,200 128.19 US$153,828
2026-05-12 2026-05-11 PlS Planned sale
3.3
Rosenbaum Michael George

Chief Executive Officer

Executive Director
1,200 -0.6%
136.38
US$163,656 		1,200 -0.6% 136.38 US$163,656
2026-05-11 2026-05-11 PrS Proposed sale
3.3
MIKE ROSENBAUM

Officer; Director

Executive Director
1,200
136.38
US$163,656 		1,200 136.38 US$163,656
2026-05-05 2026-05-04 PlS Planned sale
3.3
Rosenbaum Michael George

Chief Executive Officer

Executive Director
1,200 -0.6%
141.91
US$170,292 		1,200 -0.6% 141.91 US$170,292
2026-05-04 2026-05-04 PrS Proposed sale
3.3
MIKE ROSENBAUM

Officer; Director

Executive Director
1,200
141.91
US$170,292 		1,200 141.91 US$170,292
2026-04-27 2026-04-27 PlS Planned sale
3.3
Rosenbaum Michael George

Chief Executive Officer

Executive Director
1,200 -0.6%
138.09
US$165,708 		1,200 -0.6% 138.09 US$165,708
2026-04-27 2026-04-27 PrS Proposed sale
3.3
MIKE ROSENBAUM

Officer; Director

Executive Director
1,200
138.09
US$165,708 		1,200 138.09 US$165,708
2026-04-20 2026-04-20 PlS Planned sale
3.3
Rosenbaum Michael George

Chief Executive Officer

Executive Director
1,200 -0.6%
139.75
US$167,700 		1,200 -0.6% 139.75 US$167,700
2026-04-20 2026-04-20 PrS Proposed sale
3.3
MIKE ROSENBAUM

Officer; Director

Executive Director
1,200
139.75
US$167,700 		1,200 139.75 US$167,700
2026-04-13 2026-04-13 PlS Planned sale
3.3
Rosenbaum Michael George

Chief Executive Officer

Executive Director
1,200 -0.6%
118.77
US$142,524 		1,200 -0.6% 118.77 US$142,524
2026-04-13 2026-04-13 PrS Proposed sale
3.3
MIKE ROSENBAUM

Officer; Director

Executive Director
1,200
118.77
US$142,524 		1,200 118.77 US$142,524
2026-04-06 2026-04-06 PlS Planned sale
3.3
Rosenbaum Michael George

Chief Executive Officer

Executive Director
1,200 -0.5%
151.14
US$181,368 		1,200 -0.5% 151.14 US$181,368
2026-04-06 2026-04-06 PrS Proposed sale
3.3
MIKE ROSENBAUM

Officer; Director

Executive Director
1,200
151.14
US$181,368 		1,200 151.14 US$181,368
2026-03-31 2026-03-30 PlS Planned sale
3.3
Rosenbaum Michael George

Chief Executive Officer

Executive Director
1,200 -0.5%
145.74
US$174,888 		1,200 -0.5% 145.74 US$174,888
2026-03-30 2026-03-30 PrS Proposed sale
3.3
MIKE ROSENBAUM

Officer; Director

Executive Director
1,200
145.74
US$174,888 		1,200 145.74 US$174,888
2026-03-24 2026-03-23 PlS Planned sale
3.3
Rosenbaum Michael George

Chief Executive Officer

Executive Director
1,200 -0.5%
155.56
US$186,672 		1,200 -0.5% 155.56 US$186,672
2026-03-23 2026-03-23 PrS Proposed sale
3.3
MIKE ROSENBAUM

Officer; Director

Executive Director
1,200
155.56
US$186,672 		1,200 155.56 US$186,672
2026-03-18 2026-03-17 S Sale
3.3
Peterson David Franklin

Chief Accounting Officer

Officer
273 -2.1%
163.86
US$44,733 		273 -2.1% 163.86 US$44,733
2026-03-18 2026-03-17 S Sale
3.1
King James Winston

Chief Admin Officer, Gen Couns

Officer
1,001 -3.0%
163.86
US$164,022 		1,001 -3.0% 163.86 US$164,022
2026-03-18 2026-03-17 S Sale
3.3
Cooper Jeffrey Elliott

Chief Financial Officer

Officer
1,935 -2.8%
163.86
US$317,065 		1,935 -2.8% 163.86 US$317,065
2026-03-18 2026-03-17 S Sale
3.3
Mullen John P

President

Officer
6,576 -4.6%
163.86
US$1,077,530 		6,576 -4.6% 163.86 US$1,077,530
2026-03-18 2026-03-17 S Sale
3.3
Rosenbaum Michael George

Chief Executive Officer

Executive Director
4,737 -2.1%
163.86
US$776,195 		4,737 -2.1% 163.86 US$776,195
2026-03-17 2026-03-17 PrS Proposed sale
3.3
David F. Peterson

Chief Accounting Officer

Officer
273
163.86
US$44,733 		273 163.86 US$44,733
2026-03-17 2026-03-17 PrS Proposed sale
3.1
James Winston King

Chief Administrative Officer and General Counsel

Officer
1,001
163.86
US$164,022 		1,001 163.86 US$164,022
2026-03-17 2026-03-17 PrS Proposed sale
3.3
John P. Mullen

President
6,576
163.86
US$1,077,529 		6,576 163.86 US$1,077,529
2026-03-17 2026-03-17 PrS Proposed sale
3.3
Jeffrey Elliott Cooper

Chief Financial Officer

Officer
1,935
163.86
US$317,065 		1,935 163.86 US$317,065
2026-03-17 2026-03-17 PrS Proposed sale
3.3
Michael G. Rosenbaum

Chief Executive Officer

Officer
4,737
163.86
US$776,195 		4,737 163.86 US$776,195
2026-03-17 2026-03-16 PlS Planned sale
3.3
Rosenbaum Michael George

Chief Executive Officer

Executive Director
1,200 -0.5%
160.00
US$192,000 		1,200 -0.5% 160.00 US$192,000
2026-03-16 2026-03-16 PrS Proposed sale
3.3
MIKE ROSENBAUM

Officer; Director

Executive Director
1,200
160.00
US$192,000 		1,200 160.00 US$192,000
2026-03-13 2026-03-13 PrS Proposed sale
3.3
JEFFREY COOPER

Officer

Officer
4,757
158.72
US$755,031 		4,757 158.72 US$755,031
2026-03-13 2026-03-13 PlS Planned sale
3.3
Cooper Jeffrey Elliott

Chief Financial Officer

Officer
4,757 -6.5%
158.72
US$755,031 		4,757 -6.5% 158.72 US$755,031
2026-03-09 2026-03-09 PlS Planned sale
3.3
Rosenbaum Michael George

Chief Executive Officer

Executive Director
1,200 -0.5%
166.34
US$199,608 		1,200 -0.5% 166.34 US$199,608
2026-03-09 2026-03-09 PrS Proposed sale
3.3
MIKE ROSENBAUM

Officer; Director

Executive Director
1,200
166.34
US$199,608 		1,200 166.34 US$199,608
2026-03-03 2026-03-02 PlS Planned sale
3.3
Rosenbaum Michael George

Chief Executive Officer

Executive Director
1,200 -0.5%
143.87
US$172,644 		1,200 -0.5% 143.87 US$172,644
2026-03-02 2026-03-02 PrS Proposed sale
3.3
MIKE ROSENBAUM

Officer; Director

Executive Director
1,200
143.87
US$172,644 		1,200 143.87 US$172,644
2026-02-23 2026-02-23 PlS Planned sale
3.3
Rosenbaum Michael George

Chief Executive Officer

Executive Director
1,200 -0.5%
125.50
US$150,600 		1,200 -0.5% 125.50 US$150,600
2026-02-23 2026-02-23 PrS Proposed sale
3.3
MIKE ROSENBAUM

Officer; Director

Executive Director
1,200
125.50
US$150,600 		1,200 125.50 US$150,600
2026-02-17 2026-02-17 PlS Planned sale
3.3
Rosenbaum Michael George

Chief Executive Officer

Executive Director
1,200 -0.5%
127.00
US$152,400 		1,200 -0.5% 127.00 US$152,400
2026-02-17 2026-02-17 PrS Proposed sale
3.3
MIKE ROSENBAUM

Officer; Director

Executive Director
1,200
127.00
US$152,400 		1,200 127.00 US$152,400
2026-02-10 2026-02-09 PlS Planned sale
3.3
Rosenbaum Michael George

Chief Executive Officer

Executive Director
1,200 -0.5%
127.77
US$153,324 		1,200 -0.5% 127.77 US$153,324
2026-02-09 2026-02-09 PrS Proposed sale
3.3
MIKE ROSENBAUM

Officer; Director

Executive Director
1,200
127.77
US$153,324 		1,200 127.77 US$153,324
2026-02-04 2026-02-04 PrS Proposed sale
2.4
Lavin Paul

Former Director

Non-Executive Director
4,878
125.64
US$612,872 		4,878 125.64 US$612,872
2026-02-03 2026-02-02 PlS Planned sale
3.3
Rosenbaum Michael George

Chief Executive Officer

Executive Director
1,200 -0.5%
140.01
US$168,012 		1,200 -0.5% 140.01 US$168,012
2026-02-02 2026-02-02 PrS Proposed sale
3.3
MIKE ROSENBAUM

Officer; Director

Executive Director
1,200
140.01
US$168,012 		1,200 140.01 US$168,012
2026-01-26 2026-01-26 PrS Proposed sale
3.3
MIKE ROSENBAUM

Officer; Director

Executive Director
1,200
160.32
US$192,384 		1,200 160.32 US$192,384
2026-01-26 2026-01-26 PlS Planned sale
3.3
Rosenbaum Michael George

Chief Executive Officer

Executive Director
1,200 -0.5%
160.32
US$192,384 		1,200 -0.5% 160.32 US$192,384
2026-01-22 2026-01-20 PlS Planned sale
3.3
Rosenbaum Michael George

Chief Executive Officer

Executive Director
1,200 -0.5%
156.26
US$187,512 		1,200 -0.5% 156.26 US$187,512
2026-01-20 2026-01-20 PrS Proposed sale
3.3
MIKE ROSENBAUM

Officer; Director

Executive Director
1,200
156.26
US$187,512 		1,200 156.26 US$187,512
2026-01-15 2026-01-13 PlS Planned sale
3.3
Cooper Jeffrey Elliott

Chief Financial Officer

Officer
216 -0.3%
180.87
US$39,068 		216 -0.3% 180.87 US$39,068
2026-01-15 2026-01-13 PlS Planned sale
3.3
Rosenbaum Michael George

Chief Executive Officer

Executive Director
1,200 -0.5%
180.87
US$217,044 		1,200 -0.5% 180.87 US$217,044
2026-01-13 2026-01-13 PrS Proposed sale
3.3
JEFFREY COOPER

Officer

Officer
216
180.87
US$39,068 		216 180.87 US$39,068
2026-01-13 2026-01-13 PrS Proposed sale
3.3
MIKE ROSENBAUM

Officer; Director

Executive Director
1,200
180.87
US$217,044 		1,200 180.87 US$217,044
2025-12-29 2025-12-29 PrS Proposed sale
3.3
MIKE ROSENBAUM

Officer; Director

Executive Director
1,400
204.95
US$286,930 		1,400 204.95 US$286,930
2025-12-29 2025-12-29 PlS Planned sale
3.3
Rosenbaum Michael George

Chief Executive Officer

Executive Director
1,400 -0.6%
204.95
US$286,930 		1,400 -0.6% 204.95 US$286,930
2025-12-22 2025-12-22 PrS Proposed sale
3.3
MIKE ROSENBAUM

Officer; Director

Executive Director
1,400
200.72
US$281,008 		1,400 200.72 US$281,008
2025-12-22 2025-12-22 PlS Planned sale
3.3
Rosenbaum Michael George

Chief Executive Officer

Executive Director
1,400 -0.6%
200.72
US$281,008 		1,400 -0.6% 200.72 US$281,008
2025-12-18 2025-12-18 PrS Proposed sale
3.3
JEFFREY COOPER

Officer

Officer
1,232
195.00
US$240,240 		1,232 195.00 US$240,240
2025-12-18 2025-12-18 PrS Proposed sale
3.1
JAMES W KING

Officer

Officer
1,860
195.00
US$362,700 		1,860 195.00 US$362,700
2025-12-18 2025-12-18 PlS Planned sale
3.3
Cooper Jeffrey Elliott

Chief Financial Officer

Officer
1,232 -1.7%
195.00
US$240,240 		1,232 -1.7% 195.00 US$240,240
2025-12-18 2025-12-18 PlS Planned sale
3.1
King James Winston

Chief Admin Officer, Gen Couns

Officer
1,860 -5.2%
195.00
US$362,700 		1,860 -5.2% 195.00 US$362,700
2025-12-18 2025-12-16 S Sale
3.3
Cooper Jeffrey Elliott

Chief Financial Officer

Officer
2,872 -3.7%
192.08
US$551,643 		2,872 -3.7% 192.08 US$551,643
2025-12-18 2025-12-16 S Sale
3.1
King James Winston

Chief Admin Officer, Gen Couns

Officer
1,457 -3.9%
192.08
US$279,855 		1,457 -3.9% 192.08 US$279,855
2025-12-17 2025-12-16 S Sale
3.3
Rosenbaum Michael George

Chief Executive Officer

Executive Director
6,015 -2.4%
192.08
US$1,155,338 		6,015 -2.4% 192.08 US$1,155,338
2025-12-17 2025-12-16 S Sale
3.3
Peterson David Franklin

Chief Accounting Officer

Officer
358 -2.7%
192.08
US$68,763 		358 -2.7% 192.08 US$68,763
2025-12-17 2025-12-16 S Sale
3.3
Mullen John P

President

Officer
7,975 -5.3%
192.08
US$1,531,807 		7,975 -5.3% 192.08 US$1,531,807
2025-12-16 2025-12-16 PrS Proposed sale
3.3
John P Mullen

President
7,975
192.08
US$1,531,807 		7,975 192.08 US$1,531,807
2025-12-16 2025-12-16 PrS Proposed sale
3.3
Jeffrey Elliott Cooper

Chief Financial Officer

Officer
2,872
192.08
US$551,643 		2,872 192.08 US$551,643
2025-12-16 2025-12-16 PrS Proposed sale
3.3
Michael George Rosenbaum

Chief Executive Officer

Officer
6,015
192.08
US$1,155,338 		6,015 192.08 US$1,155,338
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