diff --git a/config/dynamic_settings.yml.example b/config/dynamic_settings.yml.example
index cdf5bfae4b59..04ef3a084da6 100644
--- a/config/dynamic_settings.yml.example
+++ b/config/dynamic_settings.yml.example
@@ -137,14 +137,13 @@ development:
   store:
     canvas:
       lti-keys:
-        # these are all the same JWK but with different kid
-        # to generate a new key, run the following in a Canvas console:
+        # These are all the same JWK but with different kid.
+        # To generate a new key, run the following in a Canvas console:
         #
-        # key = OpenSSL::PKey::RSA.generate(2048)
-        # key.public_key.to_jwk(kid: Time.now.utc.iso8601).to_json
-        jwk-past.json: "{\"kty\":\"RSA\",\"e\":\"AQAB\",\"n\":\"uX1MpfEMQCBUMcj0sBYI-iFaG5Nodp3C6OlN8uY60fa5zSBd83-iIL3n_qzZ8VCluuTLfB7rrV_tiX727XIEqQ\",\"kid\":\"2018-05-18T22:33:20Z\",\"d\":\"pYwR64x-LYFtA13iHIIeEvfPTws50ZutyGfpHN-kIZz3k-xVpun2Hgu0hVKZMxcZJ9DkG8UZPqD-zTDbCmCyLQ\",\"p\":\"6OQ2bi_oY5fE9KfQOcxkmNhxDnIKObKb6TVYqOOz2JM\",\"q\":\"y-UBef95njOrqMAxJH1QPds3ltYWr8QgGgccmcATH1M\",\"dp\":\"Ol_xkL7rZgNFt_lURRiJYpJmDDPjgkDVuafIeFTS4Ic\",\"dq\":\"RtzDY5wXr5TzrwWEztLCpYzfyAuF_PZj1cfs976apsM\",\"qi\":\"XA5wnwIrwe5MwXpaBijZsGhKJoypZProt47aVCtWtPE\"}"
-        jwk-present.json: "{\"kty\":\"RSA\",\"e\":\"AQAB\",\"n\":\"uX1MpfEMQCBUMcj0sBYI-iFaG5Nodp3C6OlN8uY60fa5zSBd83-iIL3n_qzZ8VCluuTLfB7rrV_tiX727XIEqQ\",\"kid\":\"2018-06-18T22:33:20Z\",\"d\":\"pYwR64x-LYFtA13iHIIeEvfPTws50ZutyGfpHN-kIZz3k-xVpun2Hgu0hVKZMxcZJ9DkG8UZPqD-zTDbCmCyLQ\",\"p\":\"6OQ2bi_oY5fE9KfQOcxkmNhxDnIKObKb6TVYqOOz2JM\",\"q\":\"y-UBef95njOrqMAxJH1QPds3ltYWr8QgGgccmcATH1M\",\"dp\":\"Ol_xkL7rZgNFt_lURRiJYpJmDDPjgkDVuafIeFTS4Ic\",\"dq\":\"RtzDY5wXr5TzrwWEztLCpYzfyAuF_PZj1cfs976apsM\",\"qi\":\"XA5wnwIrwe5MwXpaBijZsGhKJoypZProt47aVCtWtPE\"}"
-        jwk-future.json: "{\"kty\":\"RSA\",\"e\":\"AQAB\",\"n\":\"uX1MpfEMQCBUMcj0sBYI-iFaG5Nodp3C6OlN8uY60fa5zSBd83-iIL3n_qzZ8VCluuTLfB7rrV_tiX727XIEqQ\",\"kid\":\"2018-07-18T22:33:20Z\",\"d\":\"pYwR64x-LYFtA13iHIIeEvfPTws50ZutyGfpHN-kIZz3k-xVpun2Hgu0hVKZMxcZJ9DkG8UZPqD-zTDbCmCyLQ\",\"p\":\"6OQ2bi_oY5fE9KfQOcxkmNhxDnIKObKb6TVYqOOz2JM\",\"q\":\"y-UBef95njOrqMAxJH1QPds3ltYWr8QgGgccmcATH1M\",\"dp\":\"Ol_xkL7rZgNFt_lURRiJYpJmDDPjgkDVuafIeFTS4Ic\",\"dq\":\"RtzDY5wXr5TzrwWEztLCpYzfyAuF_PZj1cfs976apsM\",\"qi\":\"XA5wnwIrwe5MwXpaBijZsGhKJoypZProt47aVCtWtPE\"}"
+        # CanvasSecurity::RSAKeyPair.new.to_jwk.to_json
+        jwk-past.json: '{"kty":"RSA","e":"AQAB","n":"uX8P5oiiQtksQO3LT4vdvobJa72bXNtxgVQAvvPBfp5M_vhJN17WQJdNrhefUVsnLkVWxnyn3JgXWACnICUDYjr6KNN2grdq6zV1cCyZz-O6NNLcwyzfcwP4-_DuMMd2ioBnbz2Z3ApTyM78HLpioWs-K7Uips3I8RgCNy_-CkXxEN4OrGc7QZ7ni8yaQ8wla-whI7VcPqxnPPMetFQGrO5lrbeMU9D6CwRMkHZvY_qpD6GLlVYG1_al2r_8Pvw02mr_qXncDyFD3J4AF3zMm-a6VqKiaeAD18T-tNEvXhZ4_kFlalshJDXKf60U4LLevo25mGY6VFiq8nIp90speQ","kid":"2024-06-04T21:16:54Z","alg":"RS256","use":"sig","d":"gBk5F9C_jT6Aiw4sWvCR32Mhcd_sjIGWruMd6MBYnWIgdetsVGqPtudF47W4dexm8FM-C7BGE9aMOF-rCk3FOm7UFqGBs9-KXIf8Y8zJI4F2M8hyX-57GOhjZ0kIlHMKb7cgtvdpa0VOetxFymkEd8ihlHlwRpTR8XzM-uOPofNhED2kJOsDrgsxoll3jeNTsgDJMH5awW73RRIt4l3n4EHxpW5RAu16SIx0_QantDBai3uj5PigQzZPhkIpj9tzOdJ4QRcl9xHU7CGxPWtiNNMTnvZmKlpQKU6P-yBCa3vDWsESlJnkCGhwBkJ13USA130DLdVY5uOvnWL50kpRIQ","p":"67v5UvVR_pVBD_aDXDof5PCI8rj9mRUv2Z6tfu5z5jIcQLtw7zpKdkX51MuDrQlQJrIij_wVFxTvlx8nsisnOsJ9SfehvKrsn4kMzmiYBXz3gAYv-qwmrcrIx4mLV3kmtlYq6c5qX4etuJrgd5SPHz8YnPo20c9eQclZoB6MZ00","q":"yXF0YevfsIjCh2ZXs2bRhNxtSc88VNQQdEy7SMvQ4xKETPmbWEx_qd8XIS7lULjylGYgcbxpSGNcv6zG19EgEOG9zJJotQDm6TA43cqm68A6D2patfIlM68pwQeuV-PcXYQk7uajESDVW3gRbiKqFpt94CJfp1mcyEA3U0zH7N0","dp":"DIKfSq3GOjKFj2lPs1dKVgYF3ou-uZ8MOQpYvsG82NyT70ODTM7VIM254ncid85kuIj_mJCSNfVgea6nlqb_n_iuWXyQ0shnYlgNm-6lErV9FQg_B5iXPOXkHeLIyE2fplGQWXQg5Qz4RTHC89WoesoIblxBCIVuxSMAZKT6Yok","dq":"j146-ZI5ctfysxEIq_sqdQe4lIZ0pt8DEvKlfGrqsSG1nV8sy4wudAT93jUVKf1nUGza_Hee6tEk6poaLvF8g-dWAOnWsbQBo8cZQekAIdt-twf3pXTAO2eYLPS9hXn7lWb-LjVhq0gV8XKj3SG4sjxaOxHbyCxEJFVnytZjl9U","qi":"mp15h3KyOLM1_yFXG42dV5hMjXCXo5x3xwCkBeI3Yw2a96ItVn0Rpib3NzjOzxxn84KHfJ_iyBuZHr6vDPh_djRPRJN_Dhi2rt3C-VdudZLPknZnEsx_kv3-H-B-C3xOtBIff3VSwMU2DyCffnonWzkWk9aE5YV4uOfLRwzu1zU"}'
+        jwk-present.json: '{"kty":"RSA","e":"AQAB","n":"uX8P5oiiQtksQO3LT4vdvobJa72bXNtxgVQAvvPBfp5M_vhJN17WQJdNrhefUVsnLkVWxnyn3JgXWACnICUDYjr6KNN2grdq6zV1cCyZz-O6NNLcwyzfcwP4-_DuMMd2ioBnbz2Z3ApTyM78HLpioWs-K7Uips3I8RgCNy_-CkXxEN4OrGc7QZ7ni8yaQ8wla-whI7VcPqxnPPMetFQGrO5lrbeMU9D6CwRMkHZvY_qpD6GLlVYG1_al2r_8Pvw02mr_qXncDyFD3J4AF3zMm-a6VqKiaeAD18T-tNEvXhZ4_kFlalshJDXKf60U4LLevo25mGY6VFiq8nIp90speQ","kid":"2024-07-04T21:16:54Z","alg":"RS256","use":"sig","d":"gBk5F9C_jT6Aiw4sWvCR32Mhcd_sjIGWruMd6MBYnWIgdetsVGqPtudF47W4dexm8FM-C7BGE9aMOF-rCk3FOm7UFqGBs9-KXIf8Y8zJI4F2M8hyX-57GOhjZ0kIlHMKb7cgtvdpa0VOetxFymkEd8ihlHlwRpTR8XzM-uOPofNhED2kJOsDrgsxoll3jeNTsgDJMH5awW73RRIt4l3n4EHxpW5RAu16SIx0_QantDBai3uj5PigQzZPhkIpj9tzOdJ4QRcl9xHU7CGxPWtiNNMTnvZmKlpQKU6P-yBCa3vDWsESlJnkCGhwBkJ13USA130DLdVY5uOvnWL50kpRIQ","p":"67v5UvVR_pVBD_aDXDof5PCI8rj9mRUv2Z6tfu5z5jIcQLtw7zpKdkX51MuDrQlQJrIij_wVFxTvlx8nsisnOsJ9SfehvKrsn4kMzmiYBXz3gAYv-qwmrcrIx4mLV3kmtlYq6c5qX4etuJrgd5SPHz8YnPo20c9eQclZoB6MZ00","q":"yXF0YevfsIjCh2ZXs2bRhNxtSc88VNQQdEy7SMvQ4xKETPmbWEx_qd8XIS7lULjylGYgcbxpSGNcv6zG19EgEOG9zJJotQDm6TA43cqm68A6D2patfIlM68pwQeuV-PcXYQk7uajESDVW3gRbiKqFpt94CJfp1mcyEA3U0zH7N0","dp":"DIKfSq3GOjKFj2lPs1dKVgYF3ou-uZ8MOQpYvsG82NyT70ODTM7VIM254ncid85kuIj_mJCSNfVgea6nlqb_n_iuWXyQ0shnYlgNm-6lErV9FQg_B5iXPOXkHeLIyE2fplGQWXQg5Qz4RTHC89WoesoIblxBCIVuxSMAZKT6Yok","dq":"j146-ZI5ctfysxEIq_sqdQe4lIZ0pt8DEvKlfGrqsSG1nV8sy4wudAT93jUVKf1nUGza_Hee6tEk6poaLvF8g-dWAOnWsbQBo8cZQekAIdt-twf3pXTAO2eYLPS9hXn7lWb-LjVhq0gV8XKj3SG4sjxaOxHbyCxEJFVnytZjl9U","qi":"mp15h3KyOLM1_yFXG42dV5hMjXCXo5x3xwCkBeI3Yw2a96ItVn0Rpib3NzjOzxxn84KHfJ_iyBuZHr6vDPh_djRPRJN_Dhi2rt3C-VdudZLPknZnEsx_kv3-H-B-C3xOtBIff3VSwMU2DyCffnonWzkWk9aE5YV4uOfLRwzu1zU"}'
+        jwk-future.json: '{"kty":"RSA","e":"AQAB","n":"uX8P5oiiQtksQO3LT4vdvobJa72bXNtxgVQAvvPBfp5M_vhJN17WQJdNrhefUVsnLkVWxnyn3JgXWACnICUDYjr6KNN2grdq6zV1cCyZz-O6NNLcwyzfcwP4-_DuMMd2ioBnbz2Z3ApTyM78HLpioWs-K7Uips3I8RgCNy_-CkXxEN4OrGc7QZ7ni8yaQ8wla-whI7VcPqxnPPMetFQGrO5lrbeMU9D6CwRMkHZvY_qpD6GLlVYG1_al2r_8Pvw02mr_qXncDyFD3J4AF3zMm-a6VqKiaeAD18T-tNEvXhZ4_kFlalshJDXKf60U4LLevo25mGY6VFiq8nIp90speQ","kid":"2024-08-04T21:16:54Z","alg":"RS256","use":"sig","d":"gBk5F9C_jT6Aiw4sWvCR32Mhcd_sjIGWruMd6MBYnWIgdetsVGqPtudF47W4dexm8FM-C7BGE9aMOF-rCk3FOm7UFqGBs9-KXIf8Y8zJI4F2M8hyX-57GOhjZ0kIlHMKb7cgtvdpa0VOetxFymkEd8ihlHlwRpTR8XzM-uOPofNhED2kJOsDrgsxoll3jeNTsgDJMH5awW73RRIt4l3n4EHxpW5RAu16SIx0_QantDBai3uj5PigQzZPhkIpj9tzOdJ4QRcl9xHU7CGxPWtiNNMTnvZmKlpQKU6P-yBCa3vDWsESlJnkCGhwBkJ13USA130DLdVY5uOvnWL50kpRIQ","p":"67v5UvVR_pVBD_aDXDof5PCI8rj9mRUv2Z6tfu5z5jIcQLtw7zpKdkX51MuDrQlQJrIij_wVFxTvlx8nsisnOsJ9SfehvKrsn4kMzmiYBXz3gAYv-qwmrcrIx4mLV3kmtlYq6c5qX4etuJrgd5SPHz8YnPo20c9eQclZoB6MZ00","q":"yXF0YevfsIjCh2ZXs2bRhNxtSc88VNQQdEy7SMvQ4xKETPmbWEx_qd8XIS7lULjylGYgcbxpSGNcv6zG19EgEOG9zJJotQDm6TA43cqm68A6D2patfIlM68pwQeuV-PcXYQk7uajESDVW3gRbiKqFpt94CJfp1mcyEA3U0zH7N0","dp":"DIKfSq3GOjKFj2lPs1dKVgYF3ou-uZ8MOQpYvsG82NyT70ODTM7VIM254ncid85kuIj_mJCSNfVgea6nlqb_n_iuWXyQ0shnYlgNm-6lErV9FQg_B5iXPOXkHeLIyE2fplGQWXQg5Qz4RTHC89WoesoIblxBCIVuxSMAZKT6Yok","dq":"j146-ZI5ctfysxEIq_sqdQe4lIZ0pt8DEvKlfGrqsSG1nV8sy4wudAT93jUVKf1nUGza_Hee6tEk6poaLvF8g-dWAOnWsbQBo8cZQekAIdt-twf3pXTAO2eYLPS9hXn7lWb-LjVhq0gV8XKj3SG4sjxaOxHbyCxEJFVnytZjl9U","qi":"mp15h3KyOLM1_yFXG42dV5hMjXCXo5x3xwCkBeI3Yw2a96ItVn0Rpib3NzjOzxxn84KHfJ_iyBuZHr6vDPh_djRPRJN_Dhi2rt3C-VdudZLPknZnEsx_kv3-H-B-C3xOtBIff3VSwMU2DyCffnonWzkWk9aE5YV4uOfLRwzu1zU"}'
 test:
   config:
     canvas:
diff --git a/docker-compose/config/dynamic_settings.yml b/docker-compose/config/dynamic_settings.yml
index 999db5d87992..62d7c3d370b4 100644
--- a/docker-compose/config/dynamic_settings.yml
+++ b/docker-compose/config/dynamic_settings.yml
@@ -41,14 +41,13 @@ development:
   store:
     canvas:
       lti-keys:
-        # these are all the same JWK but with different kid
-        # to generate a new key, run the following in a Canvas console:
+        # These are all the same JWK but with different kid.
+        # To generate a new key, run the following in a Canvas console:
         #
-        # key = OpenSSL::PKey::RSA.generate(2048)
-        # key.public_key.to_jwk(kid: Time.now.utc.iso8601).to_json
-        jwk-past.json: '{"kty":"RSA","e":"AQAB","n":"uX1MpfEMQCBUMcj0sBYI-iFaG5Nodp3C6OlN8uY60fa5zSBd83-iIL3n_qzZ8VCluuTLfB7rrV_tiX727XIEqQ","kid":"2018-05-18T22:33:20Z","d":"pYwR64x-LYFtA13iHIIeEvfPTws50ZutyGfpHN-kIZz3k-xVpun2Hgu0hVKZMxcZJ9DkG8UZPqD-zTDbCmCyLQ","p":"6OQ2bi_oY5fE9KfQOcxkmNhxDnIKObKb6TVYqOOz2JM","q":"y-UBef95njOrqMAxJH1QPds3ltYWr8QgGgccmcATH1M","dp":"Ol_xkL7rZgNFt_lURRiJYpJmDDPjgkDVuafIeFTS4Ic","dq":"RtzDY5wXr5TzrwWEztLCpYzfyAuF_PZj1cfs976apsM","qi":"XA5wnwIrwe5MwXpaBijZsGhKJoypZProt47aVCtWtPE"}'
-        jwk-present.json: '{"kty":"RSA","e":"AQAB","n":"uX1MpfEMQCBUMcj0sBYI-iFaG5Nodp3C6OlN8uY60fa5zSBd83-iIL3n_qzZ8VCluuTLfB7rrV_tiX727XIEqQ","kid":"2018-06-18T22:33:20Z","d":"pYwR64x-LYFtA13iHIIeEvfPTws50ZutyGfpHN-kIZz3k-xVpun2Hgu0hVKZMxcZJ9DkG8UZPqD-zTDbCmCyLQ","p":"6OQ2bi_oY5fE9KfQOcxkmNhxDnIKObKb6TVYqOOz2JM","q":"y-UBef95njOrqMAxJH1QPds3ltYWr8QgGgccmcATH1M","dp":"Ol_xkL7rZgNFt_lURRiJYpJmDDPjgkDVuafIeFTS4Ic","dq":"RtzDY5wXr5TzrwWEztLCpYzfyAuF_PZj1cfs976apsM","qi":"XA5wnwIrwe5MwXpaBijZsGhKJoypZProt47aVCtWtPE"}'
-        jwk-future.json: '{"kty":"RSA","e":"AQAB","n":"uX1MpfEMQCBUMcj0sBYI-iFaG5Nodp3C6OlN8uY60fa5zSBd83-iIL3n_qzZ8VCluuTLfB7rrV_tiX727XIEqQ","kid":"2018-07-18T22:33:20Z","d":"pYwR64x-LYFtA13iHIIeEvfPTws50ZutyGfpHN-kIZz3k-xVpun2Hgu0hVKZMxcZJ9DkG8UZPqD-zTDbCmCyLQ","p":"6OQ2bi_oY5fE9KfQOcxkmNhxDnIKObKb6TVYqOOz2JM","q":"y-UBef95njOrqMAxJH1QPds3ltYWr8QgGgccmcATH1M","dp":"Ol_xkL7rZgNFt_lURRiJYpJmDDPjgkDVuafIeFTS4Ic","dq":"RtzDY5wXr5TzrwWEztLCpYzfyAuF_PZj1cfs976apsM","qi":"XA5wnwIrwe5MwXpaBijZsGhKJoypZProt47aVCtWtPE"}'
+        # CanvasSecurity::RSAKeyPair.new.to_jwk.to_json
+        jwk-past.json: '{"kty":"RSA","e":"AQAB","n":"uX8P5oiiQtksQO3LT4vdvobJa72bXNtxgVQAvvPBfp5M_vhJN17WQJdNrhefUVsnLkVWxnyn3JgXWACnICUDYjr6KNN2grdq6zV1cCyZz-O6NNLcwyzfcwP4-_DuMMd2ioBnbz2Z3ApTyM78HLpioWs-K7Uips3I8RgCNy_-CkXxEN4OrGc7QZ7ni8yaQ8wla-whI7VcPqxnPPMetFQGrO5lrbeMU9D6CwRMkHZvY_qpD6GLlVYG1_al2r_8Pvw02mr_qXncDyFD3J4AF3zMm-a6VqKiaeAD18T-tNEvXhZ4_kFlalshJDXKf60U4LLevo25mGY6VFiq8nIp90speQ","kid":"2024-06-04T21:16:54Z","alg":"RS256","use":"sig","d":"gBk5F9C_jT6Aiw4sWvCR32Mhcd_sjIGWruMd6MBYnWIgdetsVGqPtudF47W4dexm8FM-C7BGE9aMOF-rCk3FOm7UFqGBs9-KXIf8Y8zJI4F2M8hyX-57GOhjZ0kIlHMKb7cgtvdpa0VOetxFymkEd8ihlHlwRpTR8XzM-uOPofNhED2kJOsDrgsxoll3jeNTsgDJMH5awW73RRIt4l3n4EHxpW5RAu16SIx0_QantDBai3uj5PigQzZPhkIpj9tzOdJ4QRcl9xHU7CGxPWtiNNMTnvZmKlpQKU6P-yBCa3vDWsESlJnkCGhwBkJ13USA130DLdVY5uOvnWL50kpRIQ","p":"67v5UvVR_pVBD_aDXDof5PCI8rj9mRUv2Z6tfu5z5jIcQLtw7zpKdkX51MuDrQlQJrIij_wVFxTvlx8nsisnOsJ9SfehvKrsn4kMzmiYBXz3gAYv-qwmrcrIx4mLV3kmtlYq6c5qX4etuJrgd5SPHz8YnPo20c9eQclZoB6MZ00","q":"yXF0YevfsIjCh2ZXs2bRhNxtSc88VNQQdEy7SMvQ4xKETPmbWEx_qd8XIS7lULjylGYgcbxpSGNcv6zG19EgEOG9zJJotQDm6TA43cqm68A6D2patfIlM68pwQeuV-PcXYQk7uajESDVW3gRbiKqFpt94CJfp1mcyEA3U0zH7N0","dp":"DIKfSq3GOjKFj2lPs1dKVgYF3ou-uZ8MOQpYvsG82NyT70ODTM7VIM254ncid85kuIj_mJCSNfVgea6nlqb_n_iuWXyQ0shnYlgNm-6lErV9FQg_B5iXPOXkHeLIyE2fplGQWXQg5Qz4RTHC89WoesoIblxBCIVuxSMAZKT6Yok","dq":"j146-ZI5ctfysxEIq_sqdQe4lIZ0pt8DEvKlfGrqsSG1nV8sy4wudAT93jUVKf1nUGza_Hee6tEk6poaLvF8g-dWAOnWsbQBo8cZQekAIdt-twf3pXTAO2eYLPS9hXn7lWb-LjVhq0gV8XKj3SG4sjxaOxHbyCxEJFVnytZjl9U","qi":"mp15h3KyOLM1_yFXG42dV5hMjXCXo5x3xwCkBeI3Yw2a96ItVn0Rpib3NzjOzxxn84KHfJ_iyBuZHr6vDPh_djRPRJN_Dhi2rt3C-VdudZLPknZnEsx_kv3-H-B-C3xOtBIff3VSwMU2DyCffnonWzkWk9aE5YV4uOfLRwzu1zU"}'
+        jwk-present.json: '{"kty":"RSA","e":"AQAB","n":"uX8P5oiiQtksQO3LT4vdvobJa72bXNtxgVQAvvPBfp5M_vhJN17WQJdNrhefUVsnLkVWxnyn3JgXWACnICUDYjr6KNN2grdq6zV1cCyZz-O6NNLcwyzfcwP4-_DuMMd2ioBnbz2Z3ApTyM78HLpioWs-K7Uips3I8RgCNy_-CkXxEN4OrGc7QZ7ni8yaQ8wla-whI7VcPqxnPPMetFQGrO5lrbeMU9D6CwRMkHZvY_qpD6GLlVYG1_al2r_8Pvw02mr_qXncDyFD3J4AF3zMm-a6VqKiaeAD18T-tNEvXhZ4_kFlalshJDXKf60U4LLevo25mGY6VFiq8nIp90speQ","kid":"2024-07-04T21:16:54Z","alg":"RS256","use":"sig","d":"gBk5F9C_jT6Aiw4sWvCR32Mhcd_sjIGWruMd6MBYnWIgdetsVGqPtudF47W4dexm8FM-C7BGE9aMOF-rCk3FOm7UFqGBs9-KXIf8Y8zJI4F2M8hyX-57GOhjZ0kIlHMKb7cgtvdpa0VOetxFymkEd8ihlHlwRpTR8XzM-uOPofNhED2kJOsDrgsxoll3jeNTsgDJMH5awW73RRIt4l3n4EHxpW5RAu16SIx0_QantDBai3uj5PigQzZPhkIpj9tzOdJ4QRcl9xHU7CGxPWtiNNMTnvZmKlpQKU6P-yBCa3vDWsESlJnkCGhwBkJ13USA130DLdVY5uOvnWL50kpRIQ","p":"67v5UvVR_pVBD_aDXDof5PCI8rj9mRUv2Z6tfu5z5jIcQLtw7zpKdkX51MuDrQlQJrIij_wVFxTvlx8nsisnOsJ9SfehvKrsn4kMzmiYBXz3gAYv-qwmrcrIx4mLV3kmtlYq6c5qX4etuJrgd5SPHz8YnPo20c9eQclZoB6MZ00","q":"yXF0YevfsIjCh2ZXs2bRhNxtSc88VNQQdEy7SMvQ4xKETPmbWEx_qd8XIS7lULjylGYgcbxpSGNcv6zG19EgEOG9zJJotQDm6TA43cqm68A6D2patfIlM68pwQeuV-PcXYQk7uajESDVW3gRbiKqFpt94CJfp1mcyEA3U0zH7N0","dp":"DIKfSq3GOjKFj2lPs1dKVgYF3ou-uZ8MOQpYvsG82NyT70ODTM7VIM254ncid85kuIj_mJCSNfVgea6nlqb_n_iuWXyQ0shnYlgNm-6lErV9FQg_B5iXPOXkHeLIyE2fplGQWXQg5Qz4RTHC89WoesoIblxBCIVuxSMAZKT6Yok","dq":"j146-ZI5ctfysxEIq_sqdQe4lIZ0pt8DEvKlfGrqsSG1nV8sy4wudAT93jUVKf1nUGza_Hee6tEk6poaLvF8g-dWAOnWsbQBo8cZQekAIdt-twf3pXTAO2eYLPS9hXn7lWb-LjVhq0gV8XKj3SG4sjxaOxHbyCxEJFVnytZjl9U","qi":"mp15h3KyOLM1_yFXG42dV5hMjXCXo5x3xwCkBeI3Yw2a96ItVn0Rpib3NzjOzxxn84KHfJ_iyBuZHr6vDPh_djRPRJN_Dhi2rt3C-VdudZLPknZnEsx_kv3-H-B-C3xOtBIff3VSwMU2DyCffnonWzkWk9aE5YV4uOfLRwzu1zU"}'
+        jwk-future.json: '{"kty":"RSA","e":"AQAB","n":"uX8P5oiiQtksQO3LT4vdvobJa72bXNtxgVQAvvPBfp5M_vhJN17WQJdNrhefUVsnLkVWxnyn3JgXWACnICUDYjr6KNN2grdq6zV1cCyZz-O6NNLcwyzfcwP4-_DuMMd2ioBnbz2Z3ApTyM78HLpioWs-K7Uips3I8RgCNy_-CkXxEN4OrGc7QZ7ni8yaQ8wla-whI7VcPqxnPPMetFQGrO5lrbeMU9D6CwRMkHZvY_qpD6GLlVYG1_al2r_8Pvw02mr_qXncDyFD3J4AF3zMm-a6VqKiaeAD18T-tNEvXhZ4_kFlalshJDXKf60U4LLevo25mGY6VFiq8nIp90speQ","kid":"2024-08-04T21:16:54Z","alg":"RS256","use":"sig","d":"gBk5F9C_jT6Aiw4sWvCR32Mhcd_sjIGWruMd6MBYnWIgdetsVGqPtudF47W4dexm8FM-C7BGE9aMOF-rCk3FOm7UFqGBs9-KXIf8Y8zJI4F2M8hyX-57GOhjZ0kIlHMKb7cgtvdpa0VOetxFymkEd8ihlHlwRpTR8XzM-uOPofNhED2kJOsDrgsxoll3jeNTsgDJMH5awW73RRIt4l3n4EHxpW5RAu16SIx0_QantDBai3uj5PigQzZPhkIpj9tzOdJ4QRcl9xHU7CGxPWtiNNMTnvZmKlpQKU6P-yBCa3vDWsESlJnkCGhwBkJ13USA130DLdVY5uOvnWL50kpRIQ","p":"67v5UvVR_pVBD_aDXDof5PCI8rj9mRUv2Z6tfu5z5jIcQLtw7zpKdkX51MuDrQlQJrIij_wVFxTvlx8nsisnOsJ9SfehvKrsn4kMzmiYBXz3gAYv-qwmrcrIx4mLV3kmtlYq6c5qX4etuJrgd5SPHz8YnPo20c9eQclZoB6MZ00","q":"yXF0YevfsIjCh2ZXs2bRhNxtSc88VNQQdEy7SMvQ4xKETPmbWEx_qd8XIS7lULjylGYgcbxpSGNcv6zG19EgEOG9zJJotQDm6TA43cqm68A6D2patfIlM68pwQeuV-PcXYQk7uajESDVW3gRbiKqFpt94CJfp1mcyEA3U0zH7N0","dp":"DIKfSq3GOjKFj2lPs1dKVgYF3ou-uZ8MOQpYvsG82NyT70ODTM7VIM254ncid85kuIj_mJCSNfVgea6nlqb_n_iuWXyQ0shnYlgNm-6lErV9FQg_B5iXPOXkHeLIyE2fplGQWXQg5Qz4RTHC89WoesoIblxBCIVuxSMAZKT6Yok","dq":"j146-ZI5ctfysxEIq_sqdQe4lIZ0pt8DEvKlfGrqsSG1nV8sy4wudAT93jUVKf1nUGza_Hee6tEk6poaLvF8g-dWAOnWsbQBo8cZQekAIdt-twf3pXTAO2eYLPS9hXn7lWb-LjVhq0gV8XKj3SG4sjxaOxHbyCxEJFVnytZjl9U","qi":"mp15h3KyOLM1_yFXG42dV5hMjXCXo5x3xwCkBeI3Yw2a96ItVn0Rpib3NzjOzxxn84KHfJ_iyBuZHr6vDPh_djRPRJN_Dhi2rt3C-VdudZLPknZnEsx_kv3-H-B-C3xOtBIff3VSwMU2DyCffnonWzkWk9aE5YV4uOfLRwzu1zU"}'
   private:
     canvas:
       auditors.yml: |
diff --git a/inst-cli/docker-compose/config/dynamic_settings.yml.erb b/inst-cli/docker-compose/config/dynamic_settings.yml.erb
index 8de1cd92d84b..61908e524c70 100644
--- a/inst-cli/docker-compose/config/dynamic_settings.yml.erb
+++ b/inst-cli/docker-compose/config/dynamic_settings.yml.erb
@@ -48,14 +48,13 @@ development:
   store:
     canvas:
       lti-keys:
-        # these are all the same JWK but with different kid
-        # to generate a new key, run the following in a Canvas console:
+        # These are all the same JWK but with different kid.
+        # To generate a new key, run the following in a Canvas console:
         #
-        # key = OpenSSL::PKey::RSA.generate(2048)
-        # key.public_key.to_jwk(kid: Time.now.utc.iso8601).to_json
-        jwk-past.json: '{"kty":"RSA","e":"AQAB","n":"uX1MpfEMQCBUMcj0sBYI-iFaG5Nodp3C6OlN8uY60fa5zSBd83-iIL3n_qzZ8VCluuTLfB7rrV_tiX727XIEqQ","kid":"2018-05-18T22:33:20Z","d":"pYwR64x-LYFtA13iHIIeEvfPTws50ZutyGfpHN-kIZz3k-xVpun2Hgu0hVKZMxcZJ9DkG8UZPqD-zTDbCmCyLQ","p":"6OQ2bi_oY5fE9KfQOcxkmNhxDnIKObKb6TVYqOOz2JM","q":"y-UBef95njOrqMAxJH1QPds3ltYWr8QgGgccmcATH1M","dp":"Ol_xkL7rZgNFt_lURRiJYpJmDDPjgkDVuafIeFTS4Ic","dq":"RtzDY5wXr5TzrwWEztLCpYzfyAuF_PZj1cfs976apsM","qi":"XA5wnwIrwe5MwXpaBijZsGhKJoypZProt47aVCtWtPE"}'
-        jwk-present.json: '{"kty":"RSA","e":"AQAB","n":"uX1MpfEMQCBUMcj0sBYI-iFaG5Nodp3C6OlN8uY60fa5zSBd83-iIL3n_qzZ8VCluuTLfB7rrV_tiX727XIEqQ","kid":"2018-06-18T22:33:20Z","d":"pYwR64x-LYFtA13iHIIeEvfPTws50ZutyGfpHN-kIZz3k-xVpun2Hgu0hVKZMxcZJ9DkG8UZPqD-zTDbCmCyLQ","p":"6OQ2bi_oY5fE9KfQOcxkmNhxDnIKObKb6TVYqOOz2JM","q":"y-UBef95njOrqMAxJH1QPds3ltYWr8QgGgccmcATH1M","dp":"Ol_xkL7rZgNFt_lURRiJYpJmDDPjgkDVuafIeFTS4Ic","dq":"RtzDY5wXr5TzrwWEztLCpYzfyAuF_PZj1cfs976apsM","qi":"XA5wnwIrwe5MwXpaBijZsGhKJoypZProt47aVCtWtPE"}'
-        jwk-future.json: '{"kty":"RSA","e":"AQAB","n":"uX1MpfEMQCBUMcj0sBYI-iFaG5Nodp3C6OlN8uY60fa5zSBd83-iIL3n_qzZ8VCluuTLfB7rrV_tiX727XIEqQ","kid":"2018-07-18T22:33:20Z","d":"pYwR64x-LYFtA13iHIIeEvfPTws50ZutyGfpHN-kIZz3k-xVpun2Hgu0hVKZMxcZJ9DkG8UZPqD-zTDbCmCyLQ","p":"6OQ2bi_oY5fE9KfQOcxkmNhxDnIKObKb6TVYqOOz2JM","q":"y-UBef95njOrqMAxJH1QPds3ltYWr8QgGgccmcATH1M","dp":"Ol_xkL7rZgNFt_lURRiJYpJmDDPjgkDVuafIeFTS4Ic","dq":"RtzDY5wXr5TzrwWEztLCpYzfyAuF_PZj1cfs976apsM","qi":"XA5wnwIrwe5MwXpaBijZsGhKJoypZProt47aVCtWtPE"}'
+        # CanvasSecurity::RSAKeyPair.new.to_jwk.to_json
+        jwk-past.json: '{"kty":"RSA","e":"AQAB","n":"uX8P5oiiQtksQO3LT4vdvobJa72bXNtxgVQAvvPBfp5M_vhJN17WQJdNrhefUVsnLkVWxnyn3JgXWACnICUDYjr6KNN2grdq6zV1cCyZz-O6NNLcwyzfcwP4-_DuMMd2ioBnbz2Z3ApTyM78HLpioWs-K7Uips3I8RgCNy_-CkXxEN4OrGc7QZ7ni8yaQ8wla-whI7VcPqxnPPMetFQGrO5lrbeMU9D6CwRMkHZvY_qpD6GLlVYG1_al2r_8Pvw02mr_qXncDyFD3J4AF3zMm-a6VqKiaeAD18T-tNEvXhZ4_kFlalshJDXKf60U4LLevo25mGY6VFiq8nIp90speQ","kid":"2024-06-04T21:16:54Z","alg":"RS256","use":"sig","d":"gBk5F9C_jT6Aiw4sWvCR32Mhcd_sjIGWruMd6MBYnWIgdetsVGqPtudF47W4dexm8FM-C7BGE9aMOF-rCk3FOm7UFqGBs9-KXIf8Y8zJI4F2M8hyX-57GOhjZ0kIlHMKb7cgtvdpa0VOetxFymkEd8ihlHlwRpTR8XzM-uOPofNhED2kJOsDrgsxoll3jeNTsgDJMH5awW73RRIt4l3n4EHxpW5RAu16SIx0_QantDBai3uj5PigQzZPhkIpj9tzOdJ4QRcl9xHU7CGxPWtiNNMTnvZmKlpQKU6P-yBCa3vDWsESlJnkCGhwBkJ13USA130DLdVY5uOvnWL50kpRIQ","p":"67v5UvVR_pVBD_aDXDof5PCI8rj9mRUv2Z6tfu5z5jIcQLtw7zpKdkX51MuDrQlQJrIij_wVFxTvlx8nsisnOsJ9SfehvKrsn4kMzmiYBXz3gAYv-qwmrcrIx4mLV3kmtlYq6c5qX4etuJrgd5SPHz8YnPo20c9eQclZoB6MZ00","q":"yXF0YevfsIjCh2ZXs2bRhNxtSc88VNQQdEy7SMvQ4xKETPmbWEx_qd8XIS7lULjylGYgcbxpSGNcv6zG19EgEOG9zJJotQDm6TA43cqm68A6D2patfIlM68pwQeuV-PcXYQk7uajESDVW3gRbiKqFpt94CJfp1mcyEA3U0zH7N0","dp":"DIKfSq3GOjKFj2lPs1dKVgYF3ou-uZ8MOQpYvsG82NyT70ODTM7VIM254ncid85kuIj_mJCSNfVgea6nlqb_n_iuWXyQ0shnYlgNm-6lErV9FQg_B5iXPOXkHeLIyE2fplGQWXQg5Qz4RTHC89WoesoIblxBCIVuxSMAZKT6Yok","dq":"j146-ZI5ctfysxEIq_sqdQe4lIZ0pt8DEvKlfGrqsSG1nV8sy4wudAT93jUVKf1nUGza_Hee6tEk6poaLvF8g-dWAOnWsbQBo8cZQekAIdt-twf3pXTAO2eYLPS9hXn7lWb-LjVhq0gV8XKj3SG4sjxaOxHbyCxEJFVnytZjl9U","qi":"mp15h3KyOLM1_yFXG42dV5hMjXCXo5x3xwCkBeI3Yw2a96ItVn0Rpib3NzjOzxxn84KHfJ_iyBuZHr6vDPh_djRPRJN_Dhi2rt3C-VdudZLPknZnEsx_kv3-H-B-C3xOtBIff3VSwMU2DyCffnonWzkWk9aE5YV4uOfLRwzu1zU"}'
+        jwk-present.json: '{"kty":"RSA","e":"AQAB","n":"uX8P5oiiQtksQO3LT4vdvobJa72bXNtxgVQAvvPBfp5M_vhJN17WQJdNrhefUVsnLkVWxnyn3JgXWACnICUDYjr6KNN2grdq6zV1cCyZz-O6NNLcwyzfcwP4-_DuMMd2ioBnbz2Z3ApTyM78HLpioWs-K7Uips3I8RgCNy_-CkXxEN4OrGc7QZ7ni8yaQ8wla-whI7VcPqxnPPMetFQGrO5lrbeMU9D6CwRMkHZvY_qpD6GLlVYG1_al2r_8Pvw02mr_qXncDyFD3J4AF3zMm-a6VqKiaeAD18T-tNEvXhZ4_kFlalshJDXKf60U4LLevo25mGY6VFiq8nIp90speQ","kid":"2024-07-04T21:16:54Z","alg":"RS256","use":"sig","d":"gBk5F9C_jT6Aiw4sWvCR32Mhcd_sjIGWruMd6MBYnWIgdetsVGqPtudF47W4dexm8FM-C7BGE9aMOF-rCk3FOm7UFqGBs9-KXIf8Y8zJI4F2M8hyX-57GOhjZ0kIlHMKb7cgtvdpa0VOetxFymkEd8ihlHlwRpTR8XzM-uOPofNhED2kJOsDrgsxoll3jeNTsgDJMH5awW73RRIt4l3n4EHxpW5RAu16SIx0_QantDBai3uj5PigQzZPhkIpj9tzOdJ4QRcl9xHU7CGxPWtiNNMTnvZmKlpQKU6P-yBCa3vDWsESlJnkCGhwBkJ13USA130DLdVY5uOvnWL50kpRIQ","p":"67v5UvVR_pVBD_aDXDof5PCI8rj9mRUv2Z6tfu5z5jIcQLtw7zpKdkX51MuDrQlQJrIij_wVFxTvlx8nsisnOsJ9SfehvKrsn4kMzmiYBXz3gAYv-qwmrcrIx4mLV3kmtlYq6c5qX4etuJrgd5SPHz8YnPo20c9eQclZoB6MZ00","q":"yXF0YevfsIjCh2ZXs2bRhNxtSc88VNQQdEy7SMvQ4xKETPmbWEx_qd8XIS7lULjylGYgcbxpSGNcv6zG19EgEOG9zJJotQDm6TA43cqm68A6D2patfIlM68pwQeuV-PcXYQk7uajESDVW3gRbiKqFpt94CJfp1mcyEA3U0zH7N0","dp":"DIKfSq3GOjKFj2lPs1dKVgYF3ou-uZ8MOQpYvsG82NyT70ODTM7VIM254ncid85kuIj_mJCSNfVgea6nlqb_n_iuWXyQ0shnYlgNm-6lErV9FQg_B5iXPOXkHeLIyE2fplGQWXQg5Qz4RTHC89WoesoIblxBCIVuxSMAZKT6Yok","dq":"j146-ZI5ctfysxEIq_sqdQe4lIZ0pt8DEvKlfGrqsSG1nV8sy4wudAT93jUVKf1nUGza_Hee6tEk6poaLvF8g-dWAOnWsbQBo8cZQekAIdt-twf3pXTAO2eYLPS9hXn7lWb-LjVhq0gV8XKj3SG4sjxaOxHbyCxEJFVnytZjl9U","qi":"mp15h3KyOLM1_yFXG42dV5hMjXCXo5x3xwCkBeI3Yw2a96ItVn0Rpib3NzjOzxxn84KHfJ_iyBuZHr6vDPh_djRPRJN_Dhi2rt3C-VdudZLPknZnEsx_kv3-H-B-C3xOtBIff3VSwMU2DyCffnonWzkWk9aE5YV4uOfLRwzu1zU"}'
+        jwk-future.json: '{"kty":"RSA","e":"AQAB","n":"uX8P5oiiQtksQO3LT4vdvobJa72bXNtxgVQAvvPBfp5M_vhJN17WQJdNrhefUVsnLkVWxnyn3JgXWACnICUDYjr6KNN2grdq6zV1cCyZz-O6NNLcwyzfcwP4-_DuMMd2ioBnbz2Z3ApTyM78HLpioWs-K7Uips3I8RgCNy_-CkXxEN4OrGc7QZ7ni8yaQ8wla-whI7VcPqxnPPMetFQGrO5lrbeMU9D6CwRMkHZvY_qpD6GLlVYG1_al2r_8Pvw02mr_qXncDyFD3J4AF3zMm-a6VqKiaeAD18T-tNEvXhZ4_kFlalshJDXKf60U4LLevo25mGY6VFiq8nIp90speQ","kid":"2024-08-04T21:16:54Z","alg":"RS256","use":"sig","d":"gBk5F9C_jT6Aiw4sWvCR32Mhcd_sjIGWruMd6MBYnWIgdetsVGqPtudF47W4dexm8FM-C7BGE9aMOF-rCk3FOm7UFqGBs9-KXIf8Y8zJI4F2M8hyX-57GOhjZ0kIlHMKb7cgtvdpa0VOetxFymkEd8ihlHlwRpTR8XzM-uOPofNhED2kJOsDrgsxoll3jeNTsgDJMH5awW73RRIt4l3n4EHxpW5RAu16SIx0_QantDBai3uj5PigQzZPhkIpj9tzOdJ4QRcl9xHU7CGxPWtiNNMTnvZmKlpQKU6P-yBCa3vDWsESlJnkCGhwBkJ13USA130DLdVY5uOvnWL50kpRIQ","p":"67v5UvVR_pVBD_aDXDof5PCI8rj9mRUv2Z6tfu5z5jIcQLtw7zpKdkX51MuDrQlQJrIij_wVFxTvlx8nsisnOsJ9SfehvKrsn4kMzmiYBXz3gAYv-qwmrcrIx4mLV3kmtlYq6c5qX4etuJrgd5SPHz8YnPo20c9eQclZoB6MZ00","q":"yXF0YevfsIjCh2ZXs2bRhNxtSc88VNQQdEy7SMvQ4xKETPmbWEx_qd8XIS7lULjylGYgcbxpSGNcv6zG19EgEOG9zJJotQDm6TA43cqm68A6D2patfIlM68pwQeuV-PcXYQk7uajESDVW3gRbiKqFpt94CJfp1mcyEA3U0zH7N0","dp":"DIKfSq3GOjKFj2lPs1dKVgYF3ou-uZ8MOQpYvsG82NyT70ODTM7VIM254ncid85kuIj_mJCSNfVgea6nlqb_n_iuWXyQ0shnYlgNm-6lErV9FQg_B5iXPOXkHeLIyE2fplGQWXQg5Qz4RTHC89WoesoIblxBCIVuxSMAZKT6Yok","dq":"j146-ZI5ctfysxEIq_sqdQe4lIZ0pt8DEvKlfGrqsSG1nV8sy4wudAT93jUVKf1nUGza_Hee6tEk6poaLvF8g-dWAOnWsbQBo8cZQekAIdt-twf3pXTAO2eYLPS9hXn7lWb-LjVhq0gV8XKj3SG4sjxaOxHbyCxEJFVnytZjl9U","qi":"mp15h3KyOLM1_yFXG42dV5hMjXCXo5x3xwCkBeI3Yw2a96ItVn0Rpib3NzjOzxxn84KHfJ_iyBuZHr6vDPh_djRPRJN_Dhi2rt3C-VdudZLPknZnEsx_kv3-H-B-C3xOtBIff3VSwMU2DyCffnonWzkWk9aE5YV4uOfLRwzu1zU"}'
   private:
     canvas:
       uuid_provisioner: