During my conversion period and beyond I read–and still do–deeply from the papal and related social magisterium and found several (27 to this point) documents that have helped me find my way through the often confusing world of Church teaching beyond the Catechism.
These documents are a superb resource for providing Catholic doctrinal knowledge during ministry to criminals.
These are entered in the order in which I read them.
#1 QUOD APOSTOLICI MUNERIS, ENCYCLICAL OF POPE LEO XIII, ON SOCIALISM, (1878) http://www.vatican.va/holy_father/leo_xiii/encyclicals/documents/hf_l-xiii_enc_28121878_quod-apostolici-muneris_en.html
#2 RERUM NOVARUM, ENCYCLICAL OF POPE LEO XIII, ON CAPITAL AND LABOR (1891) http://www.vatican.va/holy_father/leo_xiii/encyclicals/documents/hf_l-xiii_enc_15051891_rerum-novarum_en.html
#3 QUADRAGESIMO ANNO, ENCYCLICAL OF POPE PIUS XI, ON RECONSTRUCTION OF THE SOCIAL ORDER, (1931) http://www.vatican.va/holy_father/pius_xi/encyclicals/documents/hf_p-xi_enc_19310515_quadragesimo-anno_en.html
#4 VIGILANTI CURA, ENCYCLICAL LETTER OF POPE PIUS XI , ON THE MOTION PICTURE, (1936) http://www.vatican.va/holy_father/pius_xi/encyclicals/documents/hf_p-xi_enc_29061936_vigilanti-cura_en.html
#5 MATER ET MAGISTRA, ENCYCLICAL OF POPE JOHN XXIII , ON CHRISTIANITY AND SOCIAL PROGRESS (1961) http://www.vatican.va/holy_father/john_xxiii/encyclicals/documents/hf_j-xxiii_enc_15051961_mater_en.html
#6 PRESBYTERORUM ORDINIS, DECREE ON THE MINISTRY AND LIFE OF PRIESTS, POPE PAUL VI (1965) http://www.vatican.va/archive/hist_councils/ii_vatican_council/documents/vat-ii_decree_19651207_presbyterorum-ordinis_en.html
#7 POPULORUM PROGRESSIO, ENCYCLICAL OF POPE PAUL VI, ON THE DEVELOPMENT OF PEOPLES (1967) http://www.vatican.va/holy_father/paul_vi/encyclicals/documents/hf_p-vi_enc_26031967_populorum_en.html
#8 OCTOGESIMA ADVENIENS, APOSTOLIC LETTER, OF POPE PAUL VI, (1971) http://www.vatican.va/holy_father/paul_vi/apost_letters/documents/hf_p-vi_apl_19710514_octogesima-adveniens_en.html
#9 LABOREM EXERCENS, on Human Work, on the ninetieth anniversary of Rerum Novarum, Encyclical of Pope John Paul II, (1981) http://w2.vatican.va/content/john-paul-ii/en/encyclicals/documents/hf_jp-ii_enc_14091981_laborem-exercens.html
#10 POST-SYNODAL APOSTOLIC EXHORTATION, RECONCILIATION AND PENANCE, OF JOHN PAUL II, (1984) http://www.vatican.va/holy_father/john_paul_ii/apost_exhortations/documents/hf_jp-ii_exh_02121984_reconciliatio-et-paenitentia_en.html
#11 SOLLICITUDO REI SOCIALIS On Social Concern, Pope John Paul II, for the twentieth anniversary of “Populorum Progressio, (1987). http://w2.vatican.va/content/john-paul-ii/en/encyclicals/documents/hf_jp-ii_enc_30121987_sollicitudo-rei-socialis.html
#12 CHRISTIFIDELES LAICI, POST-SYNODAL APOSTOLIC EXHORTATION, OF JOHN PAUL II, ON THE VOCATION AND THE MISSION OF THE LAY FAITHFUL IN THE CHURCH AND IN THE WORLD, (1988) http://www.vatican.va/holy_father/john_paul_ii/apost_exhortations/documents/hf_jp-ii_exh_30121988_christifideles-laici_en.html
#13 Centesimus annus, Encyclical of John Paul II, on the hundredth anniversary of Rerum Novarum, (1991) http://w2.vatican.va/content/john-paul-ii/en/encyclicals/documents/hf_jp-ii_enc_01051991_centesimus-annus.html
#14 MESSAGE, HOMILY & ANGELUS, OF HIS HOLINESS, JOHN PAUL II FOR THE JUBILEE IN PRISONS (9 JULY 2000) http://www.vatican.va/jubilee_2000/jubilevents/events_jubil-prisoners_en.htm
#15 ENCYCLICAL LETTER, DEUS CARITAS EST, God is Love, OF THE SUPREME PONTIFF BENEDICT XVI, (2005) http://www.vatican.va/holy_father/benedict_xvi/encyclicals/documents/hf_ben-xvi_enc_20051225_deus-caritas-est_en.html
#16 Toward a Global Common Good, Archbishop Diarmuid Martin Marks “Laborem Exercens” Anniversary, Catholic Social Teaching and Human Work, (2006) https://www.ewtn.com/library/BISHOPS/zglobgood.htm
#17 ENCYCLICAL LETTER, SPE SALVI, OF THE SUPREME PONTIFF BENEDICT XVI ON CHRISTIAN HOPE, (2007) http://www.vatican.va/holy_father/benedict_xvi/encyclicals/documents/hf_ben-xvi_enc_20071130_spe-salvi_en.html
#18 ADDRESS OF HIS HOLINESS BENEDICT XVI, TO THE PARTICIPANTS IN THE 14th SESSION, OF THE PONTIFICAL ACADEMY OF SOCIAL SCIENCES (2008)
#19 ENCYCLICAL LETTER, CARITAS IN VERITATE, OF THE SUPREME PONTIFF, BENEDICT XVI, ON INTEGRAL HUMAN DEVELOPMENT IN CHARITY AND TRUTH (2009) http://www.vatican.va/holy_father/benedict_xvi/encyclicals/documents/hf_ben-xvi_enc_20090629_caritas-in-veritate_en.html
#20 AD CAELI REGINAM, ENCYCLICAL OF POPE PIUS XII, ON PROCLAIMING THE QUEENSHIP OF MARY (1954) http://www.vatican.va/holy_father/pius_xii/encyclicals/documents/hf_p-xii_enc_11101954_ad-caeli-reginam_en.html
#21 INGRUENTIUM MALORUM, ENCYCLICAL OF POPE PIUS XII, ON RECITING THE ROSARY (1951) http://www.vatican.va/holy_father/pius_xii/encyclicals/documents/hf_p-xii_enc_15091951_ingruentium-malorum_en.html
#22 CONSUEVERUNT ROMANI Pope Pius V (1569) http://www.ewtn.com/library/PAPALDOC/P5CONSUE.HTM
#23 Studiorum Ducem, ON ST. THOMAS AQUINAS, Encyclical of Pope Pius XI (1923) http://www.papalencyclicals.net/Pius11/P11STUDI.HTM
#24 AETERNI PATRIS, ENCYCLICAL OF POPE LEO XIII, ON THE RESTORATION OF CHRISTIAN PHILOSOPHY, (1879) http://www.vatican.va/holy_father/leo_xiii/encyclicals/documents/hf_l-xiii_enc_04081879_aeterni-patris_en.html
#25 DIVINI REDEMPTORIS, ENCYCLICAL OF POPE PIUS XI, ON ATHEISTIC COMMUNISM (1937) http://w2.vatican.va/content/pius-xi/en/encyclicals/documents/hf_p-xi_enc_19370319_divini-redemptoris.html
#26 APOSTOLIC LETTER, MULIERIS DIGNITATEM, OF THE SUPREME PONTIFF, JOHN PAUL II, ON THE DIGNITY AND VOCATION OF WOMEN ON THE OCCASION OF THE MARIAN YEAR, (1988) http://www.vatican.va/holy_father/john_paul_ii/apost_letters/documents/hf_jp-ii_apl_15081988_mulieris-dignitatem_en.html
#27 PASCENDI DOMINICI GREGIS, ENCYCLICAL OF POPE PIUS X, ON THE DOCTRINES OF THE MODERNISTS, (1907) http://w2.vatican.va/content/pius-x/en/encyclicals/documents/hf_p-x_enc_19070908_pascendi-dominici-gregis.html