Hi markewaite,
I have upgraded all the plugins which are available for upgraded and restarted post Jenkins upgrade.
Provided all the Environment details below.
Java version:
openjdk version "11.0.9.1" 2020-11-04
OpenJDK Runtime Environment (build 11.0.9.1+1-Ubuntu-0ubuntu1.18.04)
OpenJDK 64-Bit Server VM (build 11.0.9.1+1-Ubuntu-0ubuntu1.18.04, mixed mode, sharing)
Jenkins Running on Docker container
Jenkins is accessed through a reverse proxy, setup using NGINX.
Jenkins: 2.361.4
OS: Linux - 4.15.0-91-generic
—
Office-365-Connector:4.17.0
Parameterized-Remote-Trigger:3.1.6.3
ace-editor:1.1
active-directory:2.27
ansicolor:1.0.2
ant:481.v7b_09e538fcca
antisamy-markup-formatter:155.v795fb_8702324
apache-httpcomponents-client-4-api:4.5.13-138.v4e7d9a_7b_a_e61
artifact-promotion:0.5.2
artifactdeployer:1.3
artifactory:3.17.3
async-http-client:1.9.40.0
authentication-tokens:1.4
aws-credentials:191.vcb_f183ce58b_9
aws-java-sdk:1.12.287-357.vf82d85a_6eefd
aws-java-sdk-cloudformation:1.12.287-357.vf82d85a_6eefd
aws-java-sdk-codebuild:1.12.287-357.vf82d85a_6eefd
aws-java-sdk-ec2:1.12.287-357.vf82d85a_6eefd
aws-java-sdk-ecr:1.12.287-357.vf82d85a_6eefd
aws-java-sdk-ecs:1.12.287-357.vf82d85a_6eefd
aws-java-sdk-efs:1.12.287-357.vf82d85a_6eefd
aws-java-sdk-elasticbeanstalk:1.12.287-357.vf82d85a_6eefd
aws-java-sdk-iam:1.12.287-357.vf82d85a_6eefd
aws-java-sdk-logs:1.12.287-357.vf82d85a_6eefd
aws-java-sdk-minimal:1.12.287-357.vf82d85a_6eefd
aws-java-sdk-sns:1.12.287-357.vf82d85a_6eefd
aws-java-sdk-sqs:1.12.287-357.vf82d85a_6eefd
aws-java-sdk-ssm:1.12.287-357.vf82d85a_6eefd
backup-interrupt-plugin:12.vb_120b_0e8f558
badge:1.9.1
bitbucket-approval-filter:1.0.3
bitbucket-build-status-notifier:1.4.2
bitbucket-filter-project-trait:1.0
bitbucket-oauth:0.12
bitbucket-pullrequest-builder:1.5.0
bitbucket-push-and-pull-request:2.8.3
bitbucket-scm-filter-aged-refs:0.2.0
bitbucket-scm-filter-jira-validator:0.1.0
bitbucket-scm-trait-commit-skip:0.4.0
blueocean:1.25.8
blueocean-autofavorite:1.2.5
blueocean-bitbucket-pipeline:1.25.8
blueocean-commons:1.25.8
blueocean-config:1.25.8
blueocean-core-js:1.25.8
blueocean-dashboard:1.25.8
blueocean-display-url:2.4.1
blueocean-events:1.25.8
blueocean-git-pipeline:1.25.8
blueocean-github-pipeline:1.25.8
blueocean-i18n:1.25.8
blueocean-jira:1.25.8
blueocean-jwt:1.25.8
blueocean-personalization:1.25.8
blueocean-pipeline-api-impl:1.25.8
blueocean-pipeline-editor:1.25.8
blueocean-pipeline-scm-api:1.25.8
blueocean-rest:1.25.8
blueocean-rest-impl:1.25.8
blueocean-web:1.25.8
bootstrap4-api:4.6.0-5
bootstrap5-api:5.2.1-3
bouncycastle-api:2.26
branch-api:2.1051.v9985666b_f6cc
build-blocker-plugin:1.7.8
build-name-setter:2.2.0
build-pipeline-plugin:1.5.8
build-timeout:1.24
build-timestamp:1.0.3
caffeine-api:2.9.3-65.v6a_47d0f4d1fe
changes-since-last-success:0.6
checks-api:1.8.0
clamav:0.3
clone-workspace-scm:0.6
cloud-stats:254.v47891b_b_5b_6f6
cloudbees-bitbucket-branch-source:791.vb_eea_a_476405b
cloudbees-folder:6.758.vfd75d09eea_a_1
cloudshare-docker:1.1.0
command-launcher:90.v669d7ccb_7c31
commons-lang3-api:3.12.0-36.vd97de6465d5b_
commons-text-api:1.10.0-27.vb_fa_3896786a_7
conditional-buildstep:1.4.2
config-file-provider:3.11.1
configurationslicing:430.v966357576543
convert-to-pipeline:1.0
copyartifact:1.47
credentials:1189.vf61b_a_5e2f62e
credentials-binding:523.vd859a_4b_122e6
cvs:2.19.1
dashboard-view:2.466.vdfefd95a_b_f8d
declarative-pipeline-migration-assistant:1.5.2
declarative-pipeline-migration-assistant-api:1.5.2
delivery-pipeline-plugin:1.4.2
description-setter:1.10
disable-failed-job:1.15
display-url-api:2.3.6
docker-build-publish:1.4.0
docker-build-step:2.9
docker-commons:1.21
docker-compose-build-step:1.0
docker-custom-build-environment:1.7.3
docker-java-api:3.2.13-37.vf3411c9828b9
docker-plugin:1.2.10
docker-slaves:1.0.7
docker-traceability:1.2
docker-workflow:528.v7c193a_0b_e67c
dockerhub-notification:2.6.2.1
durable-task:501.ve5d4fc08b0be
echarts-api:5.4.0-1
email-ext:2.92
envinject:2.881.v37c62073ff97
envinject-api:1.199.v3ce31253ed13
environment-dashboard:1.1.10
extended-read-permission:3.2
external-monitor-job:203.v683c09d993b_9
extra-columns:1.25
favorite:2.4.1
flexible-publish:0.16.1
folder-auth:1.4
font-awesome-api:6.2.0-3
generic-webhook-trigger:1.85.2
git:4.13.0
git-changelog:3.25
git-client:3.13.0
git-server:99.va_0826a_b_cdfa_d
github:1.36.0
github-api:1.303-400.v35c2d8258028
github-branch-source:1696.v3a_7603564d04
gradle:2.1.1
greenballs:1.15.1
groovy:453.vcdb_a_c5c99890
groovy-postbuild:2.5
handlebars:3.0.8
handy-uri-templates-2-api:2.1.8-22.v77d5b_75e6953
heavy-job:1.1
htmlpublisher:1.31
http_request:1.16
icon-shim:3.0.0
image-tag-parameter:2.0
instance-identity:116.vf8f487400980
ionicons-api:31.v4757b_6987003
ivy:2.2
jackson2-api:2.13.4.20221013-295.v8e29ea_354141
jakarta-activation-api:2.0.1-2
jakarta-mail-api:2.0.1-2
javadoc:226.v71211feb_e7e9
javax-activation-api:1.2.0-5
javax-mail-api:1.6.2-8
jaxb:2.3.7-1
jdk-tool:63.v62d2fd4b_4793
jenkins-design-language:1.25.8
jersey2-api:2.37-1
jira:3.8
jira-trigger:1.0.1
jjwt-api:0.11.5-77.v646c772fddb_0
job-dsl:1.81
job-import-plugin:3.6
job-restrictions:0.8
jobConfigHistory:1176.v1b_4290db_41a_5
jobcacher:301.v06a_c88b_0fa_f8
jobcopy-builder:1.4.2
jquery:1.12.4-1
jquery-detached:1.2.1
jquery-ui:1.0.2
jquery3-api:3.6.1-2
jsch:0.1.55.61.va_e9ee26616e7
junit:1160.vf1f01a_a_ea_b_7f
last-changes:2.7.11
ldap:2.12
leastload:3.0.0
lockable-resources:2.18
mailer:438.v02c7f0a_12fa_4
mapdb-api:1.0.9-28.vf251ce40855d
matrix-auth:3.1.5
matrix-project:785.v06b_7f47b_c631
maven-plugin:3.20
mercurial:1260.vdfb_723cdcc81
metrics:4.2.10-405.v60a_9cc74e923
mina-sshd-api-common:2.9.1-44.v476733c11f82
mina-sshd-api-core:2.9.1-44.v476733c11f82
momentjs:1.1.1
multiple-scms:0.8
nested-view:1.26
next-build-number:1.8
nodelabelparameter:1.11.0
okhttp-api:4.9.3-108.v0feda04578cf
oki-docki:1.1
pam-auth:1.10
parameterized-trigger:2.45
periodic-reincarnation:1.13
permissive-script-security:0.7
persistent-build-queue-plugin:0.1.1
pipeline-build-step:2.18
pipeline-github-lib:38.v445716ea_edda_
pipeline-graph-analysis:195.v5812d95a_a_2f9
pipeline-graph-view:143.v33ca_60725f13
pipeline-groovy-lib:613.v9c41a_160233f
pipeline-input-step:456.vd8a_957db_5b_e9
pipeline-milestone-step:101.vd572fef9d926
pipeline-model-api:2.2118.v31fd5b_9944b_5
pipeline-model-declarative-agent:1.1.1
pipeline-model-definition:2.2118.v31fd5b_9944b_5
pipeline-model-extensions:2.2118.v31fd5b_9944b_5
pipeline-rest-api:2.27
pipeline-stage-step:296.v5f6908f017a_5
pipeline-stage-tags-metadata:2.2118.v31fd5b_9944b_5
pipeline-stage-view:2.27
pipeline-utility-steps:2.13.2
plain-credentials:139.ved2b_9cf7587b
plot:2.1.11
plugin-util-api:2.18.0
popper-api:1.16.1-3
popper2-api:2.11.6-2
postbuild-task:1.9
postbuildscript:3.2.0-460.va_fda_0fa_26720
preSCMbuildstep:0.3
project-description-setter:1.2
promoted-builds:892.vd6219fc0a_efb
promoted-builds-simple:1.9
pubsub-light:1.17
python:1.3
rebuild:1.34
repo:1.16.0
resource-disposer:0.20
role-strategy:562.v44e9a_e828d0e
run-condition:1.5
saferestart:0.3
scm-api:621.vda_a_b_055e58f7
script-security:1190.v65867a_a_47126
scriptler:3.5
sectioned-view:1.25
skip-notifications-trait:82.vc7780f4b_0373
snakeyaml-api:1.33-90.v80dcb_3814d35
sse-gateway:1.26
ssh-credentials:305.v8f4381501156
ssh-slaves:2.854.v7fd446b_337c9
sshd:3.249.v2dc2ea_416e33
stashNotifier:1.28
structs:324.va_f5d6774f3a_d
subversion:2.16.0
text-finder:1.21
throttle-concurrents:2.10
timestamper:1.21
token-macro:308.v4f2b_ed62b_b_16
trilead-api:2.72.v2a_3236754f73
uno-choice:2.6.4
variant:59.vf075fe829ccb
view-cloner:1.1
windows-slaves:1.8.1
workflow-aggregator:590.v6a_d052e5a_a_b_5
workflow-api:1200.v8005c684b_a_c6
workflow-basic-steps:994.vd57e3ca_46d24
workflow-cps:3536.vb_8a_6628079d5
workflow-cps-global-lib:2.19
workflow-durable-task-step:1210.va_1e5d77e122b
workflow-job:1254.v3f64639b_11dd
workflow-multibranch:716.vc692a_e52371b_
workflow-scm-step:400.v6b_89a_1317c9a_
workflow-step-api:639.v6eca_cd8c04a_a_
workflow-support:839.v35e2736cfd5c
ws-cleanup:0.43
yet-another-docker-plugin:0.2.0
Did you follow the instructions in the upgrade guides between Jenkins 2.289.1 and Jenkins 2.361.4? Especially in the instructions that state that all plugins must be upgraded to latest releases before the Jenkins upgrade, then must be upgraded to latest releases after the Jenkins upgrade? If not, please upgrade all the plugins and check the behavior.
If it still fails, then please provide the detailed list of all plugins and their versions as described in "How to report an issue"