GUENTHNER ROBERT (Chief Legal Officer) reported 1 transaction at OAK STREET HEALTH, INC.

Review the transaction codes below to understand the nature of each event.

GUENTHNER ROBERT

Filed: 5/2/2023ACC: 0000899243-23-012037

InsiderGUENTHNER ROBERTCIK 1793328

→

IssuerOAK STREET HEALTH, INC.CIK 1564406

Officer· Chief Legal Officer

Since Aug 2020

-857.89K

Net shares

Net seller

$19.08M

Total sold

Open market trades

0B · 0S

Total transactions

49K acquired · 906.89K disposed

Non-Derivative Transactions1

Common stock, $0.001 par value

Direct

D · Disposition

−489.27K

Price / share

$39.00

Trade value

$19.08M

% of position

New position

5/2/2023

489.27K→0.00

Total

Net shares

−489.27K

Net value

-$19.08M

Security	Date	Type	Shares	Price / Share	Trade Value	% of Position	Held Before	Held After
Common stock, $0.001 par value Direct	5/2/2023	D · Disposition	−489.27K	$39.00	$19.08M	New position	489.27K	0.00
Total			−489.27K		-$19.08M

Derivative Transactions5

Employee Stock Option (Right to Buy)

Direct

D · Disposition

Converts to

Common stock, $0.001 par value

220.41K shares

−220.41K

Strike price

21.00

Held after

0.00

Exercisable

—

5/2/2023

Employee Stock Option (Right to Buy)

Direct

D · Disposition

Converts to

Common stock, $0.001 par value

13.94K shares

−13.94K

Strike price

59.63

Held after

0.00

Exercisable

—

5/2/2023

Performance Stock Option (Right to Buy)

Direct

D · Disposition

Converts to

Common stock, $0.001 par value

134.27K shares

−134.27K

Strike price

15.75

Held after

0.00

Exercisable

—

5/2/2023

Performance Stock Option (Right to Buy)

Direct

A · Award

Converts to

Common stock, $0.001 par value

49K shares

+49K

Strike price

21.96

Held after

49K

Exercisable

—

5/2/2023

Performance Stock Option (Right to Buy)

Direct

D · Disposition

Converts to

Common stock, $0.001 par value

49K shares

−49K

Strike price

21.96

Held after

0.00

Exercisable

—

5/2/2023

Security	Converts To	Date	Type	Shares	Strike Price	Exercisable	Held After
Employee Stock Option (Right to Buy) Direct	Common stock, $0.001 par value220.41K shares	5/2/2023	D · Disposition	−220.41K	21.00	—	0.00
Employee Stock Option (Right to Buy) Direct	Common stock, $0.001 par value13.94K shares	5/2/2023	D · Disposition	−13.94K	59.63	—	0.00
Performance Stock Option (Right to Buy) Direct	Common stock, $0.001 par value134.27K shares	5/2/2023	D · Disposition	−134.27K	15.75	—	0.00
Performance Stock Option (Right to Buy) Direct	Common stock, $0.001 par value49K shares	5/2/2023	A · Award	+49K	21.96	—	49K
Performance Stock Option (Right to Buy) Direct	Common stock, $0.001 par value49K shares	5/2/2023	D · Disposition	−49K	21.96	—	0.00