This case is the latest in a long-run- ning effort by Adam Williams to obtain reductions in his sen- tences for crack-cocaine offenses. It relates to his 2019 appli- cation, filed pursuant to the First Step Act of 2018, Pub. L. No. 115-391, § 404 , 132 Stat. 5194 , 5222. The district court denied that motion, but we vacated its order because the court failed to calculate the amended statutory sentencing ranges 2 No. 23-2313 applicable to Williams’s convictions. Williams amplified his motion on remand, highlighting significant changes to his rec- ord and conditions of confinement that post-dated the order we vacated. Nonetheless, the district court denied Williams’s request just one day after receiving the updated motion, in an order materially identical to the first one. Applying the total- ity-of-circumstances test the Supreme Court called for in Chavez-Meza v. United States, 138 S. Ct. 1959 , 1965–66 (2018), we conclude that this was a case that required “a more com- plete explanation,” id. (citing Molina-Martinez v. United States, 136 S. Ct. 1338 , 1348 (2016)). We therefore vacate the judgment and remand again for further proceedings. I This is far from our first encounter with Williams’s sen- tence: we reviewed it on direct appeal and then four times on post-conviction review. We thus recount only the essential facts. In 2001 Williams was convicted of (1) conspiring to dis- tribute more than 50 grams of crack cocaine, 21 U.S.C. § 846 (2000), (2) distributing more than 50 grams of crack, id. § 841(b)(1)(A)(iii), and (3) distributing more than five grams of crack, id. § 841(b)(1)(B)(iii). As the then-mandatory sentenc- ing guidelines required, the district court (acting through Judge Lozano) imposed three concurrent sentences: life im- prisonment for Counts 1 and 2 and the statutory maximum 40-year term for Count 3. We dismissed Williams’s direct ap- peal. See United States v. Williams, 51 F. App’x 589 (7th Cir. 2002) (Williams I). Over the years, Williams has tried repeatedly to secure re- ductions in those sentences. Judge Lozano presided over three of Williams’s post-conviction motions for a reduced sen- tence based on retroactive amendments to the guidelines. See No. 23-2313 3 18 U.S.C. § 3582 (c)(2). The judge dismissed the first two, con- cluding that Williams continued to pose a threat to public safety, see 18 U.S.C. § 3553 (a)(2)(C), and so the original sen- tence was still appropriate. We affirmed each of those judg- ments. See United States v. Williams, 380 F. App’x 527 (7th Cir. 2010) (Williams II); United States v. Williams, No. 12-1339, 2012 WL 5951511 (7th Cir. Nov. 29, 2012) (Williams III). When Wil- liams filed his third motion, the guidelines range for Counts 1 and 2 (by then just a recommendation, see generally United States v. Booker, 543 U.S. 220 (2005)) was 235 to 293 months’ imprisonment, rather than life. In a 2015 ruling on the motion, Judge Lozano noted that “the cumulative effect of three changes to the guidelines has transformed a once-guideline sentence into a sentence that represents a significant depar- ture,” and so he granted a “small reduction” to 360 months’ imprisonment on all counts. The ruling noted that Williams’s age at the time of the offense, lack of criminal history, and self- improvement efforts while incarcerated favored the reduc- tion, but it concluded that an above-range sentence was none- theless warranted because of “the seriousness of the offense.” We affirmed. United States v. Williams, 628 F. App’x 449 (7th Cir. 2016) (Williams IV). On October 7, 2019, Williams filed a fourth motion for a reduced sentence, but this time he relied on section 404(b) of the recently enacted First Step Act. That legislation made ret- roactive the reduced statutory penalties for crack offenses es- tablished by the Fair Sentencing Act of 2010, Pub.