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United States Software & IT Services

Twilio Inc (TWLO)

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Over the last 90 days, Twilio Inc. has seen significant insider selling, with a net value of over $317 million. Executives contributed to this trend with net sales of approximately $2.65 million. Notable transactions include large planned and proposed sales by CEO Khozema Shipchandler and a substantial sale by Sachem Head Capital Management LP.
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Ticker: TWLO Exchange: NYS
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• Purchase • Sale • Planned purchase • Planned sale Net purchase Net sale Activity signal Earnings
Top insiders
Trades
Shipchandler Khozema
Chief Executive Officer
2 sales — total 200,000 USD
Planned sale 4 Jun 2026
Value US$3,683,777.85 | Price 181.99 | Shares 13,937
Proposed sale 4 Jun 2026
Value US$570,775.83 | Price 444.75 | Shares 29,210
Planned sale 1 Jun 2026
Value US$4,326,900.85 | Price 92.51 | Shares 22,610
Proposed sale 1 Jun 2026
Value US$2,989,220.24 | Price 23.55 | Shares 78,384
Sale 27 May 2026
Value US$184,140,000.00 | Price 184.14 | Shares 1,000,000
Proposed sale 27 May 2026
Value US$184,140,000.00 | Price 184.14 | Shares 1,000,000
Planned sale 26 May 2026
Value US$840,172.00 | Price 188.00 | Shares 4,469
Planned sale 26 May 2026
Value US$1,642,006.12 | Price 187.19 | Shares 8,772
Planned sale 26 May 2026
Value US$880,317.65 | Price 186.55 | Shares 4,719
Planned sale 26 May 2026
Value US$837,619.50 | Price 185.15 | Shares 4,524
Planned sale 26 May 2026
Value US$735,621.88 | Price 184.55 | Shares 3,986
Planned sale 26 May 2026
Value US$489,234.06 | Price 182.75 | Shares 2,677
Planned sale 26 May 2026
Value US$379,205.89 | Price 181.96 | Shares 2,084
Planned sale 26 May 2026
Value US$167,510.57 | Price 180.70 | Shares 927
Proposed sale 26 May 2026
Value US$5,971,687.00 | Price 185.70 | Shares 32,158
Planned sale 19 May 2026
Value US$365,600.00 | Price 200.00 | Shares 1,828
Proposed sale 19 May 2026
Value US$365,600.00 | Price 200.00 | Shares 1,828
Planned sale 15 May 2026
Value US$178,016.49 | Price 197.80 | Shares 900
Sale 15 May 2026
Value US$93,659.62 | Price 196.76 | Shares 476
Proposed sale 15 May 2026
Value US$271,676.00 | Price 197.44 | Shares 1,376
Sale 12 May 2026
Value US$130,639,500.00 | Price 193.54 | Shares 675,000
Proposed sale 12 May 2026
Value US$130,637,745.00 | Price 193.54 | Shares 675,000
Planned sale 4 May 2026
Value US$277,973.85 | Price 185.32 | Shares 1,500
Proposed sale 4 May 2026
Value US$277,974.00 | Price 185.32 | Shares 1,500
Planned sale 21 Apr 2026
Value US$32,073.70 | Price 149.18 | Shares 215
Planned sale 21 Apr 2026
Value US$236,165.00 | Price 149.00 | Shares 1,585
Proposed sale 21 Apr 2026
Value US$268,239.00 | Price 149.02 | Shares 1,800
Planned sale 6 Apr 2026
Value US$283,543.05 | Price 135.02 | Shares 2,100
Planned sale 6 Apr 2026
Value US$736,066.10 | Price 133.83 | Shares 5,500
Planned sale 6 Apr 2026
Value US$707,177.76 | Price 133.05 | Shares 5,315
Planned sale 6 Apr 2026
Value US$369,405.96 | Price 131.93 | Shares 2,800
Proposed sale 6 Apr 2026
Value US$2,096,193.00 | Price 133.39 | Shares 15,715
Planned sale 2 Apr 2026
Value US$645,682.39 | Price 127.93 | Shares 5,047
Planned sale 2 Apr 2026
Value US$551,533.43 | Price 127.02 | Shares 4,342
Proposed sale 2 Apr 2026
Value US$1,197,216.00 | Price 127.51 | Shares 9,389
Sale 31 Mar 2026
Value US$12,505.50 | Price 125.06 | Shares 100
Sale 31 Mar 2026
Value US$229,247.19 | Price 123.92 | Shares 1,850
Sale 31 Mar 2026
Value US$587,597.81 | Price 122.90 | Shares 4,781
Sale 31 Mar 2026
Value US$720,986.75 | Price 122.35 | Shares 5,893
Proposed sale 31 Mar 2026
Value US$1,550,337.00 | Price 122.81 | Shares 12,624
Sale 31 Mar 2026
Value US$12,505.00 | Price 125.05 | Shares 100
Sale 31 Mar 2026
Value US$62,178.06 | Price 124.11 | Shares 501
Sale 31 Mar 2026
Value US$238,957.53 | Price 123.30 | Shares 1,938
Sale 31 Mar 2026
Value US$697,012.72 | Price 122.45 | Shares 5,692
Proposed sale 31 Mar 2026
Value US$1,010,653.00 | Price 122.79 | Shares 8,231
Planned sale 2 Mar 2026
Value US$100,750.00 | Price 125.00 | Shares 806
Proposed sale 2 Mar 2026
Value US$100,750.00 | Price 125.00 | Shares 806
Sale 17 Feb 2026
Value US$22,202.00 | Price 111.01 | Shares 200
Sale 17 Feb 2026
Value US$91,002.73 | Price 110.57 | Shares 823
Proposed sale 17 Feb 2026
Value US$113,205.00 | Price 110.66 | Shares 1,023
Planned sale 6 Jan 2026
Value US$4,315.52 | Price 134.86 | Shares 32
Planned sale 6 Jan 2026
Value US$1,495,992.33 | Price 134.50 | Shares 11,123
Planned sale 6 Jan 2026
Value US$290,470.60 | Price 133.18 | Shares 2,181
Proposed sale 6 Jan 2026
Value US$1,790,778.00 | Price 134.28 | Shares 13,336
Planned sale 5 Jan 2026
Value US$980,751.61 | Price 135.97 | Shares 7,213
Proposed sale 5 Jan 2026
Value US$980,752.00 | Price 135.97 | Shares 7,213
Sale 31 Dec 2025
Value US$1,162,670.04 | Price 143.38 | Shares 8,109
Sale 31 Dec 2025
Value US$1,901,947.75 | Price 143.37 | Shares 13,266
Proposed sale 2 Dec 2025
Value US$129,000,000.00 | Price 129.00 | Shares 1,000,000
Sale 2 Dec 2025
Value US$129,000,000.00 | Price 129.00 | Shares 1,000,000
Planned sale 19 Nov 2025
Value US$65,902.20 | Price 120.70 | Shares 546
Proposed sale 19 Nov 2025
Value US$65,902.00 | Price 120.70 | Shares 546
Sale 17 Nov 2025
Value US$8,716.75 | Price 124.53 | Shares 70
Sale 17 Nov 2025
Value US$91,583.14 | Price 123.76 | Shares 740
Sale 17 Nov 2025
Value US$86,341.94 | Price 122.64 | Shares 704
Proposed sale 17 Nov 2025
Value US$186,642.00 | Price 123.28 | Shares 1,514
Planned sale 9 Oct 2025
Value US$924,025.00 | Price 115.00 | Shares 8,035
Proposed sale 9 Oct 2025
Value US$924,025.00 | Price 115.00 | Shares 8,035
Planned sale 3 Oct 2025
Value US$987,370.47 | Price 104.37 | Shares 9,460
Planned sale 3 Oct 2025
Value US$357,627.72 | Price 103.30 | Shares 3,462
Proposed sale 3 Oct 2025
Value US$1,344,998.00 | Price 104.09 | Shares 12,922
Sale 30 Sep 2025
Value US$661,677.79 | Price 101.07 | Shares 6,547
Sale 30 Sep 2025
Value US$539,667.34 | Price 100.44 | Shares 5,373
Sale 30 Sep 2025
Value US$174,800.38 | Price 99.26 | Shares 1,761
Sale 30 Sep 2025
Value US$406,001.40 | Price 101.07 | Shares 4,017
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 2026-06-04 PlS Planned sale
3.2
Shipchandler Khozema

Chief Executive Officer

Executive Director
13,937 -27.1%
181.99
US$3,683,778 		13,937 -27.1% 181.99 US$3,683,778
2026-06-04 2026-06-04 PrS Proposed sale
3.2
Shipchandler Khozema

Officer; Director

Executive Director
29,210
444.75
US$570,776 		29,210 444.75 US$570,776
2026-06-03 2026-06-01 PlS Planned sale
1.3
ROTTENBERG ERIKA
Non-Executive Director
22,610 +13.6%
92.51
US$4,326,901 		22,610 +13.6% 92.51 US$4,326,901
2026-06-01 2026-06-01 PrS Proposed sale
1.3
ROTTENBERG ERIKA

Director

Non-Executive Director
2,000
199.01
US$398,015 		2,000 199.01 US$398,015
2026-05-27 2026-05-27 S Sale
1.7
Stafman Andrew
Non-Executive Director
1,000,000 -61.7%
184.14
US$184,140,000 		1,000,000 -61.7% 184.14 US$184,140,000
2026-05-27 2026-05-27 PrS Proposed sale
Sachem Head Capital Management LP

Affiliate of Director

Non-Executive Director
1,000,000
184.14
US$184,140,000 		1,000,000 184.14 US$184,140,000
2026-05-28 2026-05-26 PlS Planned sale
3.2
Shipchandler Khozema

Chief Executive Officer

Executive Director
4,469 -1.9%
188.00
US$840,172 		4,469 -1.9% 188.00 US$840,172
2026-05-28 2026-05-26 PlS Planned sale
3.2
Shipchandler Khozema

Chief Executive Officer

Executive Director
8,772 -3.5%
187.19
US$1,642,006 		8,772 -3.5% 187.19 US$1,642,006
2026-05-28 2026-05-26 PlS Planned sale
3.2
Shipchandler Khozema

Chief Executive Officer

Executive Director
4,719 -1.9%
186.55
US$880,318 		4,719 -1.9% 186.55 US$880,318
2026-05-28 2026-05-26 PlS Planned sale
3.2
Shipchandler Khozema

Chief Executive Officer

Executive Director
4,524 -1.8%
185.15
US$837,620 		4,524 -1.8% 185.15 US$837,620
2026-05-28 2026-05-26 PlS Planned sale
3.2
Shipchandler Khozema

Chief Executive Officer

Executive Director
3,986 -1.5%
184.55
US$735,622 		3,986 -1.5% 184.55 US$735,622
2026-05-28 2026-05-26 PlS Planned sale
3.2
Shipchandler Khozema

Chief Executive Officer

Executive Director
2,677 -1.0%
182.75
US$489,234 		2,677 -1.0% 182.75 US$489,234
2026-05-28 2026-05-26 PlS Planned sale
3.2
Shipchandler Khozema

Chief Executive Officer

Executive Director
2,084 -0.8%
181.96
US$379,206 		2,084 -0.8% 181.96 US$379,206
2026-05-28 2026-05-26 PlS Planned sale
3.2
Shipchandler Khozema

Chief Executive Officer

Executive Director
927 -0.3%
180.70
US$167,511 		927 -0.3% 180.70 US$167,511
2026-05-26 2026-05-26 PrS Proposed sale
3.2
Shipchandler Khozema

Officer; Director

Executive Director
32,158
185.70
US$5,971,687 		32,158 185.70 US$5,971,687
2026-05-21 2026-05-19 PlS Planned sale
2.7
Viggiano Aidan

Chief Financial Officer

Officer
1,828 -1.4%
200.00
US$365,600 		1,828 -1.4% 200.00 US$365,600
2026-05-19 2026-05-19 PrS Proposed sale
2.7
Viggiano Aidan

Officer

Officer
1,828
200.00
US$365,600 		1,828 200.00 US$365,600
2026-05-19 2026-05-15 PlS Planned sale
2.7
Viggiano Aidan

Chief Financial Officer

Officer
900 -0.7%
197.80
US$178,016 		900 -0.7% 197.80 US$178,016
2026-05-19 2026-05-15 S Sale
2.7
Viggiano Aidan

Chief Financial Officer

Officer
476 -0.4%
196.76
US$93,660 		476 -0.4% 196.76 US$93,660
2026-05-15 2026-05-15 PrS Proposed sale
2.7
Viggiano Aidan

Officer

Officer
1,376
197.44
US$271,676 		1,376 197.44 US$271,676
2026-05-12 2026-05-12 S Sale
1.7
Stafman Andrew
Non-Executive Director
675,000 -29.4%
193.54
US$130,639,500 		675,000 -29.4% 193.54 US$130,639,500
2026-05-12 2026-05-12 PrS Proposed sale
Sachem Head Capital Management LP

Director, Affiliate of Director

Non-Executive Director
675,000
193.54
US$130,637,745 		675,000 193.54 US$130,637,745
2026-05-06 2026-05-04 PlS Planned sale
1.3
ROTTENBERG ERIKA
Non-Executive Director
1,500 -4.3%
185.32
US$277,974 		1,500 -4.3% 185.32 US$277,974
2026-05-04 2026-05-04 PrS Proposed sale
1.3
ROTTENBERG ERIKA

Director

Non-Executive Director
1,500
185.32
US$277,974 		1,500 185.32 US$277,974
2026-04-23 2026-04-21 PlS Planned sale
1.3
ROTTENBERG ERIKA
Non-Executive Director
215 -0.6%
149.18
US$32,074 		215 -0.6% 149.18 US$32,074
2026-04-23 2026-04-21 PlS Planned sale
1.3
ROTTENBERG ERIKA
Non-Executive Director
1,585 -4.4%
149.00
US$236,165 		1,585 -4.4% 149.00 US$236,165
2026-04-21 2026-04-21 PrS Proposed sale
1.3
ROTTENBERG ERIKA

Director

Non-Executive Director
1,800
149.02
US$268,239 		1,800 149.02 US$268,239
2026-04-08 2026-04-06 PlS Planned sale
3.2
Shipchandler Khozema

Chief Executive Officer

Executive Director
2,100 -0.9%
135.02
US$283,543 		2,100 -0.9% 135.02 US$283,543
2026-04-08 2026-04-06 PlS Planned sale
3.2
Shipchandler Khozema

Chief Executive Officer

Executive Director
5,500 -2.3%
133.83
US$736,066 		5,500 -2.3% 133.83 US$736,066
2026-04-08 2026-04-06 PlS Planned sale
3.2
Shipchandler Khozema

Chief Executive Officer

Executive Director
5,315 -2.1%
133.05
US$707,178 		5,315 -2.1% 133.05 US$707,178
2026-04-08 2026-04-06 PlS Planned sale
3.2
Shipchandler Khozema

Chief Executive Officer

Executive Director
2,800 -1.1%
131.93
US$369,406 		2,800 -1.1% 131.93 US$369,406
2026-04-06 2026-04-06 PrS Proposed sale
3.2
Shipchandler Khozema

Officer; Director

Executive Director
15,715
133.39
US$2,096,193 		15,715 133.39 US$2,096,193
2026-04-06 2026-04-02 PlS Planned sale
2.7
Viggiano Aidan

Chief Financial Officer

Officer
5,047 -3.7%
127.93
US$645,682 		5,047 -3.7% 127.93 US$645,682
2026-04-06 2026-04-02 PlS Planned sale
2.7
Viggiano Aidan

Chief Financial Officer

Officer
4,342 -3.1%
127.02
US$551,533 		4,342 -3.1% 127.02 US$551,533
2026-04-02 2026-04-02 PrS Proposed sale
2.7
Viggiano Aidan

Officer

Officer
9,389
127.51
US$1,197,216 		9,389 127.51 US$1,197,216
2026-04-02 2026-03-31 S Sale
3.2
Shipchandler Khozema

Chief Executive Officer

Executive Director
100 -0.0%
125.06
US$12,506 		100 -0.0% 125.06 US$12,506
2026-04-02 2026-03-31 S Sale
3.2
Shipchandler Khozema

Chief Executive Officer

Executive Director
1,850 -0.7%
123.92
US$229,247 		1,850 -0.7% 123.92 US$229,247
2026-04-02 2026-03-31 S Sale
3.2
Shipchandler Khozema

Chief Executive Officer

Executive Director
4,781 -1.9%
122.90
US$587,598 		4,781 -1.9% 122.90 US$587,598
2026-04-02 2026-03-31 S Sale
3.2
Shipchandler Khozema

Chief Executive Officer

Executive Director
5,893 -2.2%
122.35
US$720,987 		5,893 -2.2% 122.35 US$720,987
2026-04-02 2026-03-31 S Sale
2.7
Viggiano Aidan

Chief Financial Officer

Officer
100 -0.1%
125.05
US$12,505 		100 -0.1% 125.05 US$12,505
2026-04-02 2026-03-31 S Sale
2.7
Viggiano Aidan

Chief Financial Officer

Officer
501 -0.4%
124.11
US$62,178 		501 -0.4% 124.11 US$62,178
2026-04-02 2026-03-31 S Sale
2.7
Viggiano Aidan

Chief Financial Officer

Officer
1,938 -1.4%
123.30
US$238,958 		1,938 -1.4% 123.30 US$238,958
2026-04-02 2026-03-31 S Sale
2.7
Viggiano Aidan

Chief Financial Officer

Officer
5,692 -3.8%
122.45
US$697,013 		5,692 -3.8% 122.45 US$697,013
2026-03-31 2026-03-31 PrS Proposed sale
2.7
Viggiano Aidan

Officer

Officer
8,231
122.79
US$1,010,653 		8,231 122.79 US$1,010,653
2026-03-31 2026-03-31 PrS Proposed sale
3.2
Shipchandler Khozema

Officer; Director

Executive Director
12,624
122.81
US$1,550,337 		12,624 122.81 US$1,550,337
2026-03-04 2026-03-02 PlS Planned sale
2.7
Viggiano Aidan

Chief Financial Officer

Officer
806 -0.5%
125.00
US$100,750 		806 -0.5% 125.00 US$100,750
2026-03-02 2026-03-02 PrS Proposed sale
2.7
Viggiano Aidan

Officer

Officer
806
125.00
US$100,750 		806 125.00 US$100,750
2026-02-19 2026-02-17 S Sale
2.7
Viggiano Aidan

Chief Financial Officer

Officer
200 -0.2%
111.01
US$22,202 		200 -0.2% 111.01 US$22,202
2026-02-19 2026-02-17 S Sale
2.7
Viggiano Aidan

Chief Financial Officer

Officer
823 -0.7%
110.57
US$91,003 		823 -0.7% 110.57 US$91,003
2026-02-17 2026-02-17 PrS Proposed sale
2.7
Viggiano Aidan

Officer

Officer
1,023
110.66
US$113,205 		1,023 110.66 US$113,205
2026-01-08 2026-01-06 PlS Planned sale
3.2
Shipchandler Khozema

Chief Executive Officer

Executive Director
32 -0.0%
134.86
US$4,316 		32 -0.0% 134.86 US$4,316
2026-01-08 2026-01-06 PlS Planned sale
3.2
Shipchandler Khozema

Chief Executive Officer

Executive Director
11,123 -5.4%
134.50
US$1,495,992 		11,123 -5.4% 134.50 US$1,495,992
2026-01-08 2026-01-06 PlS Planned sale
3.2
Shipchandler Khozema

Chief Executive Officer

Executive Director
2,181 -1.1%
133.18
US$290,471 		2,181 -1.1% 133.18 US$290,471
2026-01-06 2026-01-06 PrS Proposed sale
3.2
Shipchandler Khozema

Officer; Director

Executive Director
13,336
134.28
US$1,790,778 		13,336 134.28 US$1,790,778
2026-01-07 2026-01-05 PlS Planned sale
2.7
Viggiano Aidan

Chief Financial Officer

Officer
7,213 -6.0%
135.97
US$980,752 		7,213 -6.0% 135.97 US$980,752
2026-01-05 2026-01-05 PrS Proposed sale
2.7
Viggiano Aidan

Officer

Officer
7,213
135.97
US$980,752 		7,213 135.97 US$980,752
2026-01-05 2025-12-31 S Sale
2.7
Viggiano Aidan

Chief Financial Officer

Officer
8,109 -6.4%
143.38
US$1,162,670 		8,109 -6.4% 143.38 US$1,162,670
2026-01-05 2025-12-31 S Sale
3.2
Shipchandler Khozema

Chief Executive Officer

Executive Director
13,266 -6.0%
143.37
US$1,901,948 		13,266 -6.0% 143.37 US$1,901,948
2025-12-02 2025-12-02 PrS Proposed sale
Sachem Head Capital Management LP

Director; Affiliate of Director

Non-Executive Director
1,000,000
129.00
US$129,000,000 		1,000,000 129.00 US$129,000,000
2025-12-02 2025-12-02 S Sale
1.7
Stafman Andrew
Non-Executive Director
1,000,000 -30.3%
129.00
US$129,000,000 		1,000,000 -30.3% 129.00 US$129,000,000
2025-11-21 2025-11-19 PlS Planned sale
2.7
Viggiano Aidan

Chief Financial Officer

Officer
546 -0.4%
120.70
US$65,902 		546 -0.4% 120.70 US$65,902
2025-11-19 2025-11-19 PrS Proposed sale
2.7
Viggiano Aidan

Officer

Officer
546
120.70
US$65,902 		546 120.70 US$65,902
2025-11-19 2025-11-17 S Sale
2.7
Viggiano Aidan

Chief Financial Officer

Officer
70 -0.1%
124.53
US$8,717 		70 -0.1% 124.53 US$8,717
2025-11-19 2025-11-17 S Sale
2.7
Viggiano Aidan

Chief Financial Officer

Officer
740 -0.6%
123.76
US$91,583 		740 -0.6% 123.76 US$91,583
2025-11-19 2025-11-17 S Sale
2.7
Viggiano Aidan

Chief Financial Officer

Officer
704 -0.5%
122.64
US$86,342 		704 -0.5% 122.64 US$86,342
2025-11-17 2025-11-17 PrS Proposed sale
2.7
Viggiano Aidan

Officer

Officer
1,514
123.28
US$186,642 		1,514 123.28 US$186,642
2025-10-14 2025-10-09 PlS Planned sale
2.7
Viggiano Aidan

Chief Financial Officer

Officer
8,035 -5.8%
115.00
US$924,025 		8,035 -5.8% 115.00 US$924,025
2025-10-09 2025-10-09 PrS Proposed sale
2.7
Viggiano Aidan

Officer

Officer
8,035
115.00
US$924,025 		8,035 115.00 US$924,025
2025-10-07 2025-10-03 PlS Planned sale
3.2
Shipchandler Khozema

Chief Executive Officer

Executive Director
9,460 -4.1%
104.37
US$987,370 		9,460 -4.1% 104.37 US$987,370
2025-10-07 2025-10-03 PlS Planned sale
3.2
Shipchandler Khozema

Chief Executive Officer

Executive Director
3,462 -1.5%
103.30
US$357,628 		3,462 -1.5% 103.30 US$357,628
2025-10-03 2025-10-03 PrS Proposed sale
3.2
Shipchandler Khozema

Officer; Director

Executive Director
12,922
104.09
US$1,344,998 		12,922 104.09 US$1,344,998
2025-10-02 2025-09-30 S Sale
3.2
Shipchandler Khozema

Chief Executive Officer

Executive Director
6,547 -2.7%
101.07
US$661,678 		6,547 -2.7% 101.07 US$661,678
2025-10-02 2025-09-30 S Sale
3.2
Shipchandler Khozema

Chief Executive Officer

Executive Director
5,373 -2.2%
100.44
US$539,667 		5,373 -2.2% 100.44 US$539,667
2025-10-02 2025-09-30 S Sale
3.2
Shipchandler Khozema

Chief Executive Officer

Executive Director
1,761 -0.7%
99.26
US$174,800 		1,761 -0.7% 99.26 US$174,800
2025-10-02 2025-09-30 S Sale
2.7
Viggiano Aidan

Chief Financial Officer

Officer
4,017 -2.8%
101.07
US$406,001 		4,017 -2.8% 101.07 US$406,001
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