Update not possible

I'm trying to update my OctoPrint server, but it just shows a triangle with an exclamation point stating "Update not possible" without any more information:

Am I missing something?

Yes: The logs.

When you opened this thread, there was a template and that asked for logs.

You may have a undervoltage issue.

My bad. I don't have an undervoltage issue though. Let me grab the logs and post them.

2021-01-05 09:13:12,710 - octoprint.server.heartbeat - INFO - Server heartbeat <3
2021-01-05 09:13:12,738 - octoprint.server - INFO - --- Log roll over detected ---------------------------------------------------
2021-01-05 09:13:12,738 - octoprint.server - INFO - OctoPrint 1.3.12
2021-01-05 09:13:12,741 - octoprint.plugin.core - INFO - 17 plugin(s) registered with the system:
|  Action Command Prompt Support (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/action_command_prompt
|  Announcement Plugin (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/announcements
|  Anonymous Usage Tracking (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/tracking
|  Application Keys Plugin (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/appkeys
|  Backup & Restore (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/backup
|  Core Wizard (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/corewizard
|  Creality Temperature (1.2.4) = /home/pi/oprint/local/lib/python2.7/site-packages/octoprint_CrealityTemperature
|  Creality-2x-temperature-reporting-fix (0.0.4) = /home/pi/oprint/local/lib/python2.7/site-packages/octoprint_ender3v2tempfix
|  Discovery (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/discovery
|  Error Tracking (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/errortracking
|  Force Login (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/forcelogin
|  Logging (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/logging
|  Pi Support Plugin (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/pi_support
|  Plugin Manager (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/pluginmanager
|  Printer Safety Check (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/printer_safety_check
|  Software Update (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/softwareupdate
|  Virtual Printer (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/virtual_printer
2021-01-05 09:13:12,754 - octoprint.environment - INFO - Detected environment is Python 2.7.16 under Linux (linux2). Details:
|  hardware:
|    cores: 4
|    freq: 1200.0
|    ram: 917016576
|  os:
|    id: linux
|    platform: linux2
|  plugins:
|    pi_support:
|      model: Raspberry Pi 3 Model B Rev 1.2
|      octopi_version: 0.17.0
|  python:
|    pip: 19.3.1
|    version: 2.7.16
|    virtualenv: /home/pi/oprint
2021-01-05 09:13:12,754 - octoprint.server - INFO - ------------------------------------------------------------------------------
2021-01-05 09:13:34,899 - octoprint.server.preemptive_cache - INFO - ... done in 29.85s
2021-01-05 09:13:34,901 - octoprint.server.preemptive_cache - INFO - Preemptively caching / (ui _default) for {'query_string': 'l10n=en', 'path': '/', 'base_url': 'http://192.168.1.6/'}
2021-01-05 09:13:40,586 - octoprint.server.preemptive_cache - INFO - ... done in 5.69s
2021-01-05 09:13:41,762 - octoprint.server.util.sockjs - INFO - New connection from client: ::ffff:172.20.10.1
2021-01-05 09:13:41,876 - octoprint.server.util.flask - INFO - Passively logging in user dummy from ::ffff:172.20.10.1
2021-01-05 09:13:42,977 - octoprint.plugins.announcements - INFO - Loaded channel _important from https://octoprint.org/feeds/important.xml in 0.32s
2021-01-05 09:13:43,579 - octoprint.plugins.announcements - INFO - Loaded channel _releases from https://octoprint.org/feeds/releases.xml in 0.36s
2021-01-05 09:13:43,957 - octoprint.plugins.announcements - INFO - Loaded channel _blog from https://octoprint.org/feeds/octoblog.xml in 0.31s
2021-01-05 09:13:44,407 - octoprint.plugins.announcements - INFO - Loaded channel _plugins from https://plugins.octoprint.org/feed.xml in 0.38s
2021-01-05 09:13:45,092 - octoprint.plugins.announcements - INFO - Loaded channel _octopi from https://octoprint.org/feeds/octopi.xml in 0.32s
2021-01-05 09:13:47,184 - octoprint.server.api - ERROR - Error calling SimpleApiPlugin pluginmanager
Traceback (most recent call last):
  File "/home/pi/oprint/local/lib/python2.7/site-packages/octoprint/server/api/__init__.py", line 68, in pluginData
    response = api_plugin.on_api_get(request)
  File "/home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/pluginmanager/__init__.py", line 280, in on_api_get
    if refresh_repository or not self._is_repository_cache_valid():
  File "/home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/pluginmanager/__init__.py", line 797, in _is_repository_cache_valid
    return mtime + self._repository_cache_ttl >= time.time() > mtime
TypeError: unsupported operand type(s) for +: 'NoneType' and 'int'
2021-01-05 09:13:47,234 - tornado.access - ERROR - 500 GET /api/plugin/pluginmanager (::ffff:172.20.10.1) 57.13ms
2021-01-05 09:13:48,952 - octoprint.util.pip - INFO - Using "/home/pi/oprint/bin/python2 -m pip" as command to invoke pip
2021-01-05 09:13:48,986 - octoprint.util.pip - INFO - Using "/home/pi/oprint/bin/python2 -m pip" as command to invoke pip
2021-01-05 09:13:49,059 - octoprint.util.pip - INFO - Using "/home/pi/oprint/bin/python2 -m pip" as command to invoke pip
2021-01-05 09:13:51,400 - octoprint.util.pip - ERROR - Could not detect desired output from testballoon install, got this instead: {}
2021-01-05 09:13:51,430 - octoprint.util.pip - ERROR - Cannot use this pip install, something's wrong with the python environment. Check the lines before.
2021-01-05 09:13:52,634 - octoprint.util.pip - ERROR - Could not detect desired output from testballoon install, got this instead: {}
2021-01-05 09:13:52,663 - octoprint.util.pip - ERROR - Cannot use this pip install, something's wrong with the python environment. Check the lines before.
2021-01-05 09:13:53,876 - octoprint.util.pip - ERROR - Could not detect desired output from testballoon install, got this instead: {}
2021-01-05 09:13:53,906 - octoprint.util.pip - ERROR - Cannot use this pip install, something's wrong with the python environment. Check the lines before.
2021-01-05 09:13:53,977 - octoprint.plugins.softwareupdate - INFO - Saved version cache to disk
2021-01-05 09:14:12,893 - octoprint.plugins.softwareupdate - INFO - Saved version cache to disk
2021-01-05 09:15:58,725 - octoprint.plugins.softwareupdate - INFO - Saved version cache to disk
2021-01-05 09:16:27,664 - octoprint.server.api.system - INFO - Performing command for core:restart: sudo service octoprint restart
2021-01-05 09:16:28,026 - octoprint.server - INFO - Shutting down...
2021-01-05 09:16:28,895 - octoprint.events - INFO - Processing shutdown event, this will be our last event
2021-01-05 09:16:28,903 - octoprint.events - INFO - Event loop shut down
2021-01-05 09:16:28,920 - octoprint.server - INFO - Goodbye!
2021-01-05 09:16:30,906 - octoprint.startup - INFO - ******************************************************************************
2021-01-05 09:16:30,908 - octoprint.startup - INFO - Starting OctoPrint 1.3.12
2021-01-05 09:16:30,908 - octoprint.startup - INFO - ******************************************************************************
2021-01-05 09:16:31,946 - octoprint.startup - INFO - Blacklist processing done, adding 1 blacklisted plugin versions: roomtemp (any)
2021-01-05 09:16:32,000 - octoprint.plugin.core - INFO - Loading plugins from /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins, /home/pi/.octoprint/plugins and installed plugin packages...
2021-01-05 09:16:33,310 - octoprint.plugins.errortracking - INFO - Initialized error tracking
2021-01-05 09:16:33,314 - octoprint.plugin.core - INFO - Found 17 plugin(s) providing 17 mixin implementations, 27 hook handlers
2021-01-05 09:16:33,537 - octoprint.server.heartbeat - INFO - Starting server heartbeat, 900.0s interval
2021-01-05 09:16:33,562 - octoprint.server - INFO - Intermediary server started
2021-01-05 09:16:33,563 - octoprint.plugin.core - INFO - Loading plugins from /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins, /home/pi/.octoprint/plugins and installed plugin packages...
2021-01-05 09:16:33,689 - octoprint.plugin.core - INFO - Found 17 plugin(s) providing 17 mixin implementations, 27 hook handlers
2021-01-05 09:16:33,724 - octoprint.filemanager.storage - INFO - Initializing the file metadata for /home/pi/.octoprint/uploads...
2021-01-05 09:16:34,277 - octoprint.filemanager.storage - INFO - ... file metadata for /home/pi/.octoprint/uploads initialized successfully.
2021-01-05 09:16:34,348 - octoprint.plugins.softwareupdate - INFO - Loaded version cache from disk
2021-01-05 09:16:35,443 - octoprint.util.pip - INFO - Using "/home/pi/oprint/bin/python2 -m pip" as command to invoke pip
2021-01-05 09:16:36,508 - octoprint.util.pip - INFO - Version of pip is 19.3.1
2021-01-05 09:16:36,510 - octoprint.util.pip - INFO - pip installs to /home/pi/oprint/lib/python2.7/site-packages (writable -> yes), --user flag needed -> no, virtual env -> yes
2021-01-05 09:16:36,511 - octoprint.util.pip - INFO - ==> pip ok -> yes
2021-01-05 09:16:36,516 - octoprint.plugin.core - INFO - Initialized 17 plugin implementation(s)
2021-01-05 09:16:36,528 - octoprint.plugin.core - INFO - 17 plugin(s) registered with the system:
|  Action Command Prompt Support (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/action_command_prompt
|  Announcement Plugin (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/announcements
|  Anonymous Usage Tracking (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/tracking
|  Application Keys Plugin (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/appkeys
|  Backup & Restore (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/backup
|  Core Wizard (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/corewizard
|  Creality Temperature (1.2.4) = /home/pi/oprint/local/lib/python2.7/site-packages/octoprint_CrealityTemperature
|  Creality-2x-temperature-reporting-fix (0.0.4) = /home/pi/oprint/local/lib/python2.7/site-packages/octoprint_ender3v2tempfix
|  Discovery (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/discovery
|  Error Tracking (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/errortracking
|  Force Login (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/forcelogin
|  Logging (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/logging
|  Pi Support Plugin (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/pi_support
|  Plugin Manager (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/pluginmanager
|  Printer Safety Check (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/printer_safety_check
|  Software Update (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/softwareupdate
|  Virtual Printer (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/virtual_printer
2021-01-05 09:16:36,545 - octoprint.environment - INFO - Detected environment is Python 2.7.16 under Linux (linux2). Details:
|  hardware:
|    cores: 4
|    freq: 1200.0
|    ram: 917016576
|  os:
|    id: linux
|    platform: linux2
|  plugins:
|    pi_support:
|      model: Raspberry Pi 3 Model B Rev 1.2
|      octopi_version: 0.17.0
|  python:
|    pip: 19.3.1
|    version: 2.7.16
|    virtualenv: /home/pi/oprint
2021-01-05 09:16:36,556 - octoprint.server - INFO - Reset webasset folder /home/pi/.octoprint/generated/webassets...
2021-01-05 09:16:36,574 - octoprint.server - INFO - Reset webasset folder /home/pi/.octoprint/generated/.webassets-cache...
2021-01-05 09:16:37,357 - octoprint.server - INFO - Shutting down intermediary server...
2021-01-05 09:16:37,837 - octoprint.server - INFO - Intermediary server shut down
2021-01-05 09:16:37,840 - octoprint.events - INFO - Processing startup event, this is our first event
2021-01-05 09:16:37,841 - octoprint.events - INFO - Adding 0 events to queue that were held back before startup event
2021-01-05 09:16:37,845 - octoprint.filemanager - INFO - Adding backlog items from all storage types to analysis queue...
2021-01-05 09:16:37,848 - octoprint.filemanager - INFO - Added 0 items from storage type "local" to analysis queue
2021-01-05 09:16:37,892 - octoprint.server.util.watchdog - INFO - Running initial scan on watched folder...
2021-01-05 09:16:37,895 - octoprint.server.util.watchdog - INFO - ... initial scan done.
2021-01-05 09:16:37,909 - octoprint.plugins.discovery - INFO - Registered 'OctoPrint instance "Skylar's OctoPrint"' for _http._tcp
2021-01-05 09:16:37,921 - octoprint.plugins.discovery - INFO - Registered 'OctoPrint instance "Skylar's OctoPrint"' for _octoprint._tcp
2021-01-05 09:16:37,927 - octoprint.plugins.discovery - INFO - Registered OctoPrint instance "Skylar's OctoPrint" for SSDP
2021-01-05 09:16:37,951 - octoprint.server - INFO - Listening on http://127.0.0.1:5000
2021-01-05 09:16:38,558 - octoprint.plugins.pluginmanager - INFO - Loaded plugin repository data from https://plugins.octoprint.org/plugins.json
2021-01-05 09:16:39,192 - octoprint.util.pip - INFO - Using "/home/pi/oprint/bin/python2 -m pip" as command to invoke pip
2021-01-05 09:16:39,285 - octoprint.util.pip - INFO - pip installs to /home/pi/oprint/lib/python2.7/site-packages (writable -> yes), --user flag needed -> no, virtual env -> yes
2021-01-05 09:16:39,286 - octoprint.util.pip - INFO - ==> pip ok -> yes
2021-01-05 09:16:40,574 - octoprint.plugins.pluginmanager - INFO - Loaded plugin notices data from https://plugins.octoprint.org/notices.json
2021-01-05 09:16:41,111 - octoprint.server.util.sockjs - INFO - New connection from client: ::ffff:172.20.10.1
2021-01-05 09:16:41,237 - octoprint.server.util.flask - INFO - Passively logging in user dummy from ::ffff:172.20.10.1
2021-01-05 09:16:59,119 - octoprint.server.util.flask.PreemptiveCache - INFO - Adding entry for / and {'query_string': 'l10n=en', 'path': u'/', '_count': 1, '_timestamp': 1609838219.119571, 'base_url': u'http://octopi.local/'}
2021-01-05 09:17:08,736 - octoprint.server.util.sockjs - INFO - Client connection closed: ::ffff:172.20.10.1
2021-01-05 09:17:10,037 - octoprint.server.util.sockjs - INFO - New connection from client: ::ffff:172.20.10.1
2021-01-05 09:17:10,172 - octoprint.server.util.flask - INFO - Passively logging in user dummy from ::ffff:172.20.10.1
2021-01-05 09:17:40,277 - octoprint.plugins.softwareupdate - INFO - Saved version cache to disk
2021-01-05 09:17:57,326 - octoprint.util.pip - INFO - Using "/home/pi/oprint/bin/python2 -m pip" as command to invoke pip
2021-01-05 09:17:57,376 - octoprint.util.pip - INFO - Using "/home/pi/oprint/bin/python2 -m pip" as command to invoke pip
2021-01-05 09:17:57,419 - octoprint.util.pip - INFO - Using "/home/pi/oprint/bin/python2 -m pip" as command to invoke pip
2021-01-05 09:17:58,516 - octoprint.util.pip - ERROR - Could not detect desired output from testballoon install, got this instead: {}
2021-01-05 09:17:58,551 - octoprint.util.pip - ERROR - Cannot use this pip install, something's wrong with the python environment. Check the lines before.
2021-01-05 09:17:59,735 - octoprint.util.pip - ERROR - Could not detect desired output from testballoon install, got this instead: {}
2021-01-05 09:17:59,761 - octoprint.util.pip - ERROR - Cannot use this pip install, something's wrong with the python environment. Check the lines before.
2021-01-05 09:18:00,930 - octoprint.util.pip - ERROR - Could not detect desired output from testballoon install, got this instead: {}
2021-01-05 09:18:00,956 - octoprint.util.pip - ERROR - Cannot use this pip install, something's wrong with the python environment. Check the lines before.
2021-01-05 09:18:01,016 - octoprint.plugins.softwareupdate - INFO - Saved version cache to disk
2021-01-05 09:18:15,872 - octoprint.plugins.softwareupdate - INFO - Saved version cache to disk
2021-01-05 09:20:50,368 - octoprint.plugins.softwareupdate - INFO - Saved version cache to disk
2021-01-05 09:21:45,573 - octoprint.server.api.system - INFO - Performing command for core:reboot: sudo shutdown -r now
2021-01-05 09:21:45,866 - octoprint.server.util.sockjs - INFO - Client connection closed: ::ffff:172.20.10.1
2021-01-05 09:21:46,167 - octoprint.server - INFO - Shutting down...
2021-01-05 09:21:46,328 - octoprint.events - INFO - Processing shutdown event, this will be our last event
2021-01-05 09:21:46,330 - octoprint.events - INFO - Event loop shut down
2021-01-05 09:21:46,342 - octoprint.server - INFO - Goodbye!
2021-01-05 09:21:55,743 - octoprint.startup - INFO - ******************************************************************************
2021-01-05 09:21:55,745 - octoprint.startup - INFO - Starting OctoPrint 1.3.12
2021-01-05 09:21:55,746 - octoprint.startup - INFO - ******************************************************************************
2021-01-05 09:21:56,588 - octoprint.startup - INFO - Blacklist processing done, adding 1 blacklisted plugin versions: roomtemp (any)
2021-01-05 09:21:56,690 - octoprint.plugin.core - INFO - Loading plugins from /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins, /home/pi/.octoprint/plugins and installed plugin packages...
2021-01-05 09:21:59,081 - octoprint.plugins.errortracking - INFO - Initialized error tracking
2021-01-05 09:21:59,085 - octoprint.plugin.core - INFO - Found 17 plugin(s) providing 17 mixin implementations, 27 hook handlers
2021-01-05 09:21:59,342 - octoprint.server.heartbeat - INFO - Starting server heartbeat, 900.0s interval
2021-01-05 09:22:00,755 - octoprint.server - INFO - Intermediary server started
2021-01-05 09:22:00,757 - octoprint.plugin.core - INFO - Loading plugins from /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins, /home/pi/.octoprint/plugins and installed plugin packages...
2021-01-05 09:22:00,884 - octoprint.plugin.core - INFO - Found 17 plugin(s) providing 17 mixin implementations, 27 hook handlers
2021-01-05 09:22:00,919 - octoprint.filemanager.storage - INFO - Initializing the file metadata for /home/pi/.octoprint/uploads...
2021-01-05 09:22:01,468 - octoprint.filemanager.storage - INFO - ... file metadata for /home/pi/.octoprint/uploads initialized successfully.
2021-01-05 09:22:01,543 - octoprint.plugins.softwareupdate - INFO - Loaded version cache from disk
2021-01-05 09:22:02,856 - octoprint.util.pip - INFO - Using "/home/pi/oprint/bin/python2 -m pip" as command to invoke pip
2021-01-05 09:22:03,929 - octoprint.util.pip - INFO - Version of pip is 19.3.1
2021-01-05 09:22:03,931 - octoprint.util.pip - INFO - pip installs to /home/pi/oprint/lib/python2.7/site-packages (writable -> yes), --user flag needed -> no, virtual env -> yes
2021-01-05 09:22:03,932 - octoprint.util.pip - INFO - ==> pip ok -> yes
2021-01-05 09:22:03,937 - octoprint.plugin.core - INFO - Initialized 17 plugin implementation(s)
2021-01-05 09:22:03,948 - octoprint.plugin.core - INFO - 17 plugin(s) registered with the system:
|  Action Command Prompt Support (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/action_command_prompt
|  Announcement Plugin (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/announcements
|  Anonymous Usage Tracking (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/tracking
|  Application Keys Plugin (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/appkeys
|  Backup & Restore (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/backup
|  Core Wizard (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/corewizard
|  Creality Temperature (1.2.4) = /home/pi/oprint/local/lib/python2.7/site-packages/octoprint_CrealityTemperature
|  Creality-2x-temperature-reporting-fix (0.0.4) = /home/pi/oprint/local/lib/python2.7/site-packages/octoprint_ender3v2tempfix
|  Discovery (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/discovery
|  Error Tracking (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/errortracking
|  Force Login (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/forcelogin
|  Logging (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/logging
|  Pi Support Plugin (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/pi_support
|  Plugin Manager (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/pluginmanager
|  Printer Safety Check (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/printer_safety_check
|  Software Update (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/softwareupdate
|  Virtual Printer (bundled) = /home/pi/oprint/lib/python2.7/site-packages/octoprint/plugins/virtual_printer
2021-01-05 09:22:03,967 - octoprint.environment - INFO - Detected environment is Python 2.7.16 under Linux (linux2). Details:
|  hardware:
|    cores: 4
|    freq: 1200.0
|    ram: 917016576
|  os:
|    id: linux
|    platform: linux2
|  plugins:
|    pi_support:
|      model: Raspberry Pi 3 Model B Rev 1.2
|      octopi_version: 0.17.0
|  python:
|    pip: 19.3.1
|    version: 2.7.16
|    virtualenv: /home/pi/oprint
2021-01-05 09:22:03,979 - octoprint.server - INFO - Reset webasset folder /home/pi/.octoprint/generated/webassets...
2021-01-05 09:22:03,999 - octoprint.server - INFO - Reset webasset folder /home/pi/.octoprint/generated/.webassets-cache...
2021-01-05 09:22:04,938 - octoprint.server - INFO - Shutting down intermediary server...
2021-01-05 09:22:05,341 - octoprint.server - INFO - Intermediary server shut down
2021-01-05 09:22:05,344 - octoprint.events - INFO - Processing startup event, this is our first event
2021-01-05 09:22:05,345 - octoprint.events - INFO - Adding 0 events to queue that were held back before startup event
2021-01-05 09:22:05,348 - octoprint.filemanager - INFO - Adding backlog items from all storage types to analysis queue...
2021-01-05 09:22:05,384 - octoprint.filemanager - INFO - Added 0 items from storage type "local" to analysis queue
2021-01-05 09:22:05,397 - octoprint.server.util.watchdog - INFO - Running initial scan on watched folder...
2021-01-05 09:22:05,400 - octoprint.server.util.watchdog - INFO - ... initial scan done.
2021-01-05 09:22:05,414 - octoprint.plugins.discovery - INFO - Registered 'OctoPrint instance "Skylar's OctoPrint"' for _http._tcp
2021-01-05 09:22:05,427 - octoprint.plugins.discovery - INFO - Registered 'OctoPrint instance "Skylar's OctoPrint"' for _octoprint._tcp
2021-01-05 09:22:05,464 - octoprint.server - INFO - Listening on http://127.0.0.1:5000
2021-01-05 09:22:05,607 - octoprint.plugins.pluginmanager - INFO - Loaded plugin repository data from disk, was still valid
2021-01-05 09:22:06,585 - octoprint.plugins.pluginmanager - INFO - Loaded notice data from disk, was still valid
2021-01-05 09:22:06,750 - octoprint.util.pip - INFO - Using "/home/pi/oprint/bin/python2 -m pip" as command to invoke pip
2021-01-05 09:22:06,751 - octoprint.util.pip - INFO - pip installs to /home/pi/oprint/lib/python2.7/site-packages (writable -> yes), --user flag needed -> no, virtual env -> yes
2021-01-05 09:22:06,753 - octoprint.util.pip - INFO - ==> pip ok -> yes
2021-01-05 09:22:07,037 - octoprint.server.preemptive_cache - INFO - Preemptively caching / (ui _default) for {'query_string': 'l10n=en', 'path': '/', 'base_url': 'http://octopi.local/'}
2021-01-05 09:22:24,016 - octoprint.server.preemptive_cache - INFO - ... done in 16.98s
2021-01-05 09:24:08,929 - octoprint.server.util.sockjs - INFO - New connection from client: fe80::10cd:e61b:e8ec:3954
2021-01-05 09:24:09,108 - octoprint.server.util.flask - INFO - Passively logging in user dummy from fe80::10cd:e61b:e8ec:3954
2021-01-05 09:25:05,974 - octoprint.server.util.sockjs - INFO - New connection from client: fe80::10cd:e61b:e8ec:3954
2021-01-05 09:25:06,054 - octoprint.server.util.flask - INFO - Passively logging in user dummy from fe80::10cd:e61b:e8ec:3954
2021-01-05 09:25:07,466 - octoprint.server.util.sockjs - INFO - Client connection closed: fe80::10cd:e61b:e8ec:3954
2021-01-05 09:25:07,499 - octoprint.server.util.sockjs - INFO - Client connection closed: fe80::10cd:e61b:e8ec:3954
2021-01-05 09:25:52,957 - octoprint.server.util.sockjs - INFO - New connection from client: fe80::10cd:e61b:e8ec:3954
2021-01-05 09:25:53,074 - octoprint.server.util.flask - INFO - Passively logging in user dummy from fe80::10cd:e61b:e8ec:3954
2021-01-05 09:31:30,810 - octoprint.server.util.sockjs - INFO - New connection from client: fe80::10cd:e61b:e8ec:3954
2021-01-05 09:31:30,936 - octoprint.server.util.flask - INFO - Passively logging in user dummy from fe80::10cd:e61b:e8ec:3954
2021-01-05 09:31:33,038 - octoprint.server.util.sockjs - INFO - Client connection closed: fe80::10cd:e61b:e8ec:3954
2021-01-05 09:32:37,128 - octoprint.util.pip - INFO - Using "/home/pi/oprint/bin/python2 -m pip" as command to invoke pip
2021-01-05 09:32:37,320 - octoprint.util.pip - INFO - Using "/home/pi/oprint/bin/python2 -m pip" as command to invoke pip
2021-01-05 09:32:37,322 - octoprint.util.pip - INFO - Using "/home/pi/oprint/bin/python2 -m pip" as command to invoke pip
2021-01-05 09:32:38,408 - octoprint.util.pip - ERROR - Could not detect desired output from testballoon install, got this instead: {}
2021-01-05 09:32:38,440 - octoprint.util.pip - ERROR - Cannot use this pip install, something's wrong with the python environment. Check the lines before.
2021-01-05 09:32:39,635 - octoprint.util.pip - ERROR - Could not detect desired output from testballoon install, got this instead: {}
2021-01-05 09:32:39,663 - octoprint.util.pip - ERROR - Cannot use this pip install, something's wrong with the python environment. Check the lines before.
2021-01-05 09:32:40,859 - octoprint.util.pip - ERROR - Could not detect desired output from testballoon install, got this instead: {}
2021-01-05 09:32:40,888 - octoprint.util.pip - ERROR - Cannot use this pip install, something's wrong with the python environment. Check the lines before.
2021-01-05 09:32:40,952 - octoprint.plugins.softwareupdate - INFO - Saved version cache to disk
2021-01-05 09:32:45,488 - octoprint.plugins.softwareupdate - INFO - Saved version cache to disk
2021-01-05 09:34:56,715 - octoprint.plugins.backup - INFO - Creating backup zip at /home/pi/.octoprint/data/backup/.octoprint-backup-20210105-093456.zip (excluded: -)...
2021-01-05 09:34:58,761 - octoprint.plugins.backup - INFO - ... done creating backup zip.
2021-01-05 09:36:59,344 - octoprint.server.heartbeat - INFO - Server heartbeat <3
2021-01-05 09:41:56,254 - octoprint.server.util.sockjs - INFO - New connection from client: fe80::10cd:e61b:e8ec:3954
2021-01-05 09:41:56,335 - octoprint.server.util.flask - INFO - Passively logging in user dummy from fe80::10cd:e61b:e8ec:3954

If you haven't already, try this FAQ:

Looks like it can't find pip to update, see if that fixes it.

Otherwise, head to SSH and run this command to manually update,

~/oprint/bin/pip install octoprint==1.5.2

I had issues with pip before, but the trick only applies to the Plugin Manager, apparently. It was the first thing I tried myself this morning. Any more thoughts?

EDIT: sorry, missed your second comment, will try now.

Not working...

Traceback (most recent call last):
  File "/home/pi/oprint/bin/pip", line 10, in <module>
    sys.exit(main())
  File "/home/pi/oprint/local/lib/python2.7/site-packages/pip/_internal/main.py", line 45, in main
    command = create_command(cmd_name, isolated=("--isolated" in cmd_args))
  File "/home/pi/oprint/local/lib/python2.7/site-packages/pip/_internal/commands/__init__.py", line 96, in create_command
    module = importlib.import_module(module_path)
  File "/usr/lib/python2.7/importlib/__init__.py", line 37, in import_module
    __import__(name)
  File "/home/pi/oprint/local/lib/python2.7/site-packages/pip/_internal/commands/install.py", line 20, in <module>
    from pip._internal.cache import WheelCache
  File "/home/pi/oprint/local/lib/python2.7/site-packages/pip/_internal/cache.py", line 19, in <module>
    from pip._internal.wheel import InvalidWheelFilename, Wheel
  File "/home/pi/oprint/local/lib/python2.7/site-packages/pip/_internal/wheel.py", line 26, in <module>
    from pip._vendor.distlib.scripts import ScriptMaker
  File "/home/pi/oprint/local/lib/python2.7/site-packages/pip/_vendor/distlib/scripts.py", line 15, in <module>
    from .resources import finder
  File "/home/pi/oprint/local/lib/python2.7/site-packages/pip/_vendor/distlib/resources.py", line 20, in <module>
    from .util import cached_property, get_cache_base, path_to_cache_dir, Cache
EOFError: EOF read where object expected

EOF means end of file, but it was unexpected, so hinting at some sort of corruption or general brokenness in the install. I recommend trying to flash it to the SD card again, if you can still get into OctoPrint make a backup and then you should be able to restore it on a fresh flash.

Yeah, OctoPrint works fine, so will do. Thanks!

EDIT: running smooth again. Wasn't able to restore backup of settings though. It complained about users.yaml not being there. But a fresh setup is always good.