SQL Server 2014

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CREATE TABLE [SESSION] (
    START_DATE DATE,
    END_DATE DATE,
    PAID DECIMAL(18,2),
    SESSION_ID INT,
    SESSION_TYPE INT,
    SESSION_ENTER_DATE DATE
);

INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('4/13/2016', '4/26/2016', '32.53', '7415', '3256', '4/20/2016');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('4/27/2016', '5/10/2016', '32.53', '7415', '3256', '5/3/2016');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('5/11/2016', '5/24/2016', '32.53', '7415', '3256', '5/13/2016');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('11/11/2017', '12/8/2017', '43.59', '7415', '4963', '12/5/2017');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('12/9/2017', '1/5/2018', '43.59', '7415', '4963', '1/3/2018');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('1/6/2018', '2/2/2018', '43.59', '7415', '4963', '1/12/2018');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('2/3/2018', '3/2/2018', '43.59', '7415', '4963', '2/16/2018');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('3/31/2018', '4/27/2018', '43.59', '7415', '4963', '4/17/2018');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('6/23/2018', '7/20/2018', '43.59', '7415', '4963', '7/5/2018');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('7/21/2018', '8/17/2018', '43.59', '7415', '4963', '8/7/2018');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('8/18/2018', '9/14/2018', '43.59', '7415', '4963', '9/10/2018');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('9/15/2018', '10/12/2018', '43.59', '7415', '4963', '9/27/2018');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('10/13/2018', '11/9/2018', '43.59', '7415', '4963', '10/26/2018');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('12/9/2018', '12/28/2018', '37.02', '7415', '4963', '11/29/2018');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('12/29/2018', '12/29/2018', '63.6', '7415', '4963', '1/2/2019');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('2/17/2022', '3/2/2022', '48.58', '8642', '3256', '2/25/2022');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('2/17/2022', '5/12/2022', '29.27', '8642', '3256', '7/27/2022');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('3/3/2022', '3/9/2022', '46.6', '8642', '3256', '3/7/2022');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('3/10/2022', '3/16/2022', '46.6', '8642', '3256', '3/14/2022');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('3/17/2022', '3/23/2022', '46.6', '8642', '3256', '3/21/2022');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('3/24/2022', '3/30/2022', '46.6', '8642', '3256', '3/28/2022');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('3/31/2022', '4/6/2022', '46.6', '8642', '3256', '4/4/2022');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('4/7/2022', '4/13/2022', '46.6', '8642', '3256', '4/11/2022');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('4/14/2022', '4/20/2022', '46.6', '8642', '3256', '4/18/2022');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('4/21/2022', '4/27/2022', '46.6', '8642', '3256', '4/25/2022');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('4/28/2022', '5/4/2022', '46.6', '8642', '3256', '5/10/2022');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('5/5/2022', '5/11/2022', '46.6', '8642', '3256', '5/10/2022');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('5/12/2022', '5/12/2022', '109.8', '8642', '3256', '5/13/2022');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('6/2/2022', '6/15/2022', '85.2', '8642', '3256', '6/17/2022');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('6/2/2022', '7/27/2022', '48.72', '8642', '3256', '7/27/2022');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('6/16/2022', '6/22/2022', '46.6', '8642', '3256', '6/17/2022');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('6/23/2022', '6/29/2022', '46.6', '8642', '3256', '6/27/2022');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('6/30/2022', '7/6/2022', '46.6', '8642', '3256', '7/4/2022');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('7/7/2022', '7/13/2022', '46.6', '8642', '3256', '7/11/2022');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('7/14/2022', '7/20/2022', '46.6', '8642', '3256', '7/18/2022');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('7/21/2022', '7/27/2022', '46.6', '8642', '3256', '7/25/2022');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('7/28/2022', '8/3/2022', '61.19', '8642', '3256', '8/1/2022');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('8/4/2022', '8/10/2022', '61.19', '8642', '3256', '8/8/2022');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('8/11/2022', '8/17/2022', '61.19', '8642', '3256', '8/15/2022');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('8/18/2022', '8/24/2022', '61.19', '8642', '3256', '8/22/2022');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('8/25/2022', '8/31/2022', '61.19', '8642', '3256', '8/29/2022');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('9/1/2022', '9/7/2022', '61.19', '8642', '3256', '9/5/2022');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('4/19/2023', '4/25/2023', '61.19', '8642', '3256', '4/19/2023');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('4/26/2023', '5/2/2023', '61.19', '8642', '3256', '4/24/2023');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('5/3/2023', '5/9/2023', '61.19', '8642', '3256', '5/1/2023');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('5/10/2023', '5/16/2023', '61.19', '8642', '3256', '5/8/2023');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('5/17/2023', '5/23/2023', '61.19', '8642', '3256', '5/15/2023');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('5/24/2023', '5/30/2023', '61.19', '8642', '3256', '5/22/2023');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('5/31/2023', '6/6/2023', '61.19', '8642', '3256', '5/23/2023');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('6/7/2023', '6/13/2023', '61.19', '8642', '3256', '6/2/2023');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('1/2/2024', '1/8/2024', '17.48', '8642', '3256', '1/3/2024');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('1/2/2024', '1/7/2024', '34.97', '8642', '3256', '1/19/2024');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('2/22/2024', '4/11/2024', '18', '8642', '4963', '3/29/2024');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('4/12/2024', '4/18/2024', '71', '8642', '4963', '4/13/2024');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('4/19/2024', '4/25/2024', '71', '8642', '4963', '4/19/2024');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('4/26/2024', '5/2/2024', '71', '8642', '4963', '4/27/2024');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('5/3/2024', '5/9/2024', '71', '8642', '4963', '5/6/2024');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('5/10/2024', '5/16/2024', '71', '8642', '4963', '5/10/2024');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('5/17/2024', '5/23/2024', '71', '8642', '4963', '5/20/2024');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('5/24/2024', '5/30/2024', '71', '8642', '4963', '5/24/2024');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('5/31/2024', '6/6/2024', '71', '8642', '4963', '6/3/2024');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('6/7/2024', '6/13/2024', '71', '8642', '4963', '6/7/2024');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('6/14/2024', '6/20/2024', '71', '8642', '4963', '6/14/2024');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('6/21/2024', '6/27/2024', '71', '8642', '4963', '6/21/2024');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('6/28/2024', '7/4/2024', '71', '8642', '4963', '6/28/2024');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('7/5/2024', '7/11/2024', '71', '8642', '4963', '7/5/2024');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('7/12/2024', '7/18/2024', '71', '8642', '4963', '7/12/2024');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('7/19/2024', '7/25/2024', '71', '8642', '4963', '7/19/2024');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('7/26/2024', '8/1/2024', '71', '8642', '4963', '7/26/2024');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('8/2/2024', '8/8/2024', '71', '8642', '4963', '8/2/2024');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('8/9/2024', '8/15/2024', '71', '8642', '4963', '8/9/2024');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('8/16/2024', '8/22/2024', '71', '8642', '4963', '8/16/2024');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('8/23/2024', '8/29/2024', '71', '8642', '4963', '8/23/2024');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('8/30/2024', '9/5/2024', '71', '8642', '4963', '8/30/2024');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('9/6/2024', '9/12/2024', '71', '8642', '4963', '9/6/2024');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('9/13/2024', '9/19/2024', '71', '8642', '4963', '9/13/2024');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('9/20/2024', '9/26/2024', '71', '8642', '4963', '9/20/2024');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('9/27/2024', '10/3/2024', '71', '8642', '4963', '9/27/2024');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('10/4/2024', '10/10/2024', '71', '8642', '4963', '10/4/2024');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('10/11/2024', '10/17/2024', '71', '8642', '4963', '10/11/2024');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('10/18/2024', '10/31/2024', '48', '8642', '4963', '10/31/2024');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('11/1/2024', '11/7/2024', '71', '8642', '4963', '10/30/2024');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('11/8/2024', '11/14/2024', '71', '8642', '4963', '11/9/2024');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('11/15/2024', '11/21/2024', '71', '8642', '4963', '11/16/2024');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('11/22/2024', '11/28/2024', '71', '8642', '4963', '11/21/2024');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('11/29/2024', '12/5/2024', '71', '8642', '4963', '11/26/2024');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('12/6/2024', '12/12/2024', '71', '8642', '4963', '12/7/2024');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('12/13/2024', '12/19/2024', '71', '8642', '4963', '12/14/2024');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('12/20/2024', '12/26/2024', '71', '8642', '4963', NULL);
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('12/20/2024', '12/26/2024', '71', '8642', '4963', NULL);
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('12/20/2024', '12/26/2024', '71', '8642', '3256', '12/25/2024');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('12/20/2024', '12/26/2024', '71', '8642', '4963', '12/25/2024');
INSERT INTO SESSION (START_DATE, END_DATE, PAID, SESSION_ID, SESSION_TYPE, SESSION_ENTER_DATE) VALUES ('12/27/2024', '1/2/2025', '71', '8642', '4963', '12/25/2024');

WITH tmp AS (
        SELECT 
        a.*,
        ROW_NUMBER() OVER (
            PARTITION BY SESSION_ID, SESSION_TYPE, START_DATE 
            ORDER BY SESSION_ENTER_DATE DESC
        ) AS rn
    FROM [SESSION] a
),
base AS (
    SELECT *
    FROM tmp
    WHERE rn = 1
),
cte AS (
    SELECT 
        SESSION_ID,
        SESSION_TYPE,
        CONVERT(date, START_DATE, 101) AS sdate,
        CONVERT(date, END_DATE, 101)   AS edate,
        PAID,
        CONVERT(date, SESSION_ENTER_DATE, 101) AS sessdate
    FROM base
),
cte_with_flag AS (
    SELECT 
        *,
        CASE 
            WHEN sdate > DATEADD(day, 1,
                   ISNULL(LAG(edate) OVER (
                        PARTITION BY SESSION_ID, SESSION_TYPE 
                        ORDER BY sdate
                   ), sdate))
            THEN 1 
            ELSE 0 
        END AS new_grp_flag
    FROM cte
),
cte_grouping AS (
    SELECT 
        *,
        SUM(new_grp_flag) OVER (
            PARTITION BY SESSION_ID, SESSION_TYPE 
            ORDER BY sdate 
            ROWS UNBOUNDED PRECEDING
        ) AS grp
    FROM cte_with_flag
),
cte_agg AS (
    SELECT 
        SESSION_ID,
        SESSION_TYPE,
        grp,
        MIN(sdate) AS start_date,
        MAX(edate) AS end_date
    FROM cte_grouping
    GROUP BY SESSION_ID, SESSION_TYPE, grp
)
SELECT 
    CONVERT(VARCHAR(10), a.start_date, 23) AS START_DATE,
    CONVERT(VARCHAR(10), a.end_date, 23)   AS END_DATE,
    g.PAID,
    a.SESSION_ID,
    a.SESSION_TYPE,
    CONVERT(VARCHAR(10), g.sessdate, 23)   AS SESSION_ENTER_DATE
FROM cte_agg a
INNER JOIN cte_grouping g
    ON a.SESSION_ID   = g.SESSION_ID
   AND a.SESSION_TYPE = g.SESSION_TYPE
   AND a.grp        = g.grp
   AND a.start_date = g.sdate  
ORDER BY a.SESSION_ID, a.start_date;

START_DATE	END_DATE	PAID	SESSION_ID	SESSION_TYPE	SESSION_ENTER_DATE
2016-04-13	2016-05-24	32.53	7415	3256	2016-04-20
2017-11-11	2018-03-02	43.59	7415	4963	2017-12-05
2018-03-31	2018-04-27	43.59	7415	4963	2018-04-17
2018-06-23	2018-11-09	43.59	7415	4963	2018-07-05
2018-12-09	2018-12-29	37.02	7415	4963	2018-11-29
2022-02-17	2022-05-12	29.27	8642	3256	2022-07-27
2022-06-02	2022-09-07	48.72	8642	3256	2022-07-27
2023-04-19	2023-06-13	61.19	8642	3256	2023-04-19
2024-01-02	2024-01-07	34.97	8642	3256	2024-01-19
2024-02-22	2025-01-02	18.00	8642	4963	2024-03-29
2024-12-20	2024-12-26	71.00	8642	3256	2024-12-25