I just generated new server certs (deleted existing and restart teddy cloud), see logs below. Then I flashed the new ca.der to the Toniebox (I flashed the download from web UI, also checked ´diff´ with my backup server/cert/ca.der), logs below.
Logs teddy clouds
Running teddycloud...
TeddyCloud v0.6.4 (f13703a) - 2025-03-05 08:01:37 +0000 ubuntu linux-armv7l(32)
INFO |settings.c:0860:settings_load_ovl| Load settings from /teddycloud/config/config.overlay.ini
INFO |settings.c:0860:settings_load_ovl| Load settings from /teddycloud/config/config.ini
ERROR|tls_adapter.c:0189:read_certificate| Failed to open '/teddycloud/certs/server/ca-root.pem' for cert type detection
ERROR|tls_adapter.c:0376:load_cert| Loading cert '/teddycloud/certs/server/ca-root.pem' failed
INFO |settings.c:1670:settings_load_certs_id| ********************************************
INFO |settings.c:1671:settings_load_certs_id| No certificates found. Generating.
INFO |settings.c:1672:settings_load_certs_id| This will take several minutes...
INFO |settings.c:1673:settings_load_certs_id| ********************************************
ERROR|tls_adapter.c:0189:read_certificate| Failed to open '/teddycloud/certs/server/ca-root.pem' for cert type detection
ERROR|tls_adapter.c:0376:load_cert| Loading cert '/teddycloud/certs/server/ca-root.pem' failed
ERROR|tls_adapter.c:0189:read_certificate| Failed to open '/teddycloud/certs/server/ca-key.pem' for cert type detection
ERROR|tls_adapter.c:0376:load_cert| Loading cert '/teddycloud/certs/server/ca-key.pem' failed
INFO |cert.c:0437:cert_generate_default| Generating CA certificate...
INFO |cert.c:0042:cert_generate_rsa| Generating RSA Key... (slow, very slow!!!)
INFO |tls_adapter.c:0204:read_certificate| File '/teddycloud/certs/server/ca-root.pem' assumed PEM style
INFO |tls_adapter.c:0201:read_certificate| File '/teddycloud/certs/server/ca-key.pem' detected as DER style RSA PRIVATE KEY
ERROR|tls_adapter.c:0189:read_certificate| Failed to open '/teddycloud/certs/server/teddy-cert.pem' for cert type detection
ERROR|tls_adapter.c:0376:load_cert| Loading cert '/teddycloud/certs/server/teddy-cert.pem' failed
INFO |cert.c:0471:cert_generate_default| Generating Server certificate...
INFO |cert.c:0079:cert_load_ca| Load CA certificate...
INFO |cert.c:0103:cert_load_ca| Load CA key...
INFO |cert.c:0042:cert_generate_rsa| Generating RSA Key... (slow, very slow!!!)
INFO |tls_adapter.c:0204:read_certificate| File '/teddycloud/certs/server/ca-root.pem' assumed PEM style
INFO |tls_adapter.c:0201:read_certificate| File '/teddycloud/certs/server/ca-key.pem' detected as DER style RSA PRIVATE KEY
INFO |tls_adapter.c:0204:read_certificate| File '/teddycloud/certs/server/teddy-cert.pem' assumed PEM style
INFO |tls_adapter.c:0201:read_certificate| File '/teddycloud/certs/server/teddy-key.pem' detected as DER style RSA PRIVATE KEY
INFO |tls_adapter.c:0197:read_certificate| File '/teddycloud/certs/client/ca.der' detected as DER style CERTIFICATE
INFO |tls_adapter.c:0197:read_certificate| File '/teddycloud/certs/client/client.der' detected as DER style CERTIFICATE
INFO |tls_adapter.c:0201:read_certificate| File '/teddycloud/certs/client/private.der' detected as DER style RSA PRIVATE KEY
INFO |settings.c:1675:settings_load_certs_id| ********************************************
INFO |settings.c:1676:settings_load_certs_id| FINISHED
INFO |settings.c:1677:settings_load_certs_id| ********************************************
INFO |settings.c:0860:settings_load_ovl| Load settings from /teddycloud/config/config.overlay.ini
INFO |tls_adapter.c:0390:tls_adapter_init| Loading certificates...
INFO |tls_adapter.c:0204:read_certificate| File '/teddycloud/certs/server/ca-root.pem' assumed PEM style
INFO |tls_adapter.c:0201:read_certificate| File '/teddycloud/certs/server/ca-key.pem' detected as DER style RSA PRIVATE KEY
INFO |tls_adapter.c:0204:read_certificate| File '/teddycloud/certs/server/teddy-cert.pem' assumed PEM style
INFO |tls_adapter.c:0201:read_certificate| File '/teddycloud/certs/server/teddy-key.pem' detected as DER style RSA PRIVATE KEY
INFO |tls_adapter.c:0197:read_certificate| File '/teddycloud/certs/client/ca.der' detected as DER style CERTIFICATE
INFO |tls_adapter.c:0197:read_certificate| File '/teddycloud/certs/client/client.der' detected as DER style CERTIFICATE
INFO |tls_adapter.c:0201:read_certificate| File '/teddycloud/certs/client/private.der' detected as DER style RSA PRIVATE KEY
==8==ERROR: AddressSanitizer: out of memory: failed to allocate 0xb09000 (11571200) bytes of FakeStack (error code: 12)
ERROR|server.c:0877:server_init| ERROR: Failed to mmap
httpServerStart() for HTTPS failed with code 101
Running teddycloud...
TeddyCloud v0.6.4 (f13703a) - 2025-03-05 08:01:37 +0000 ubuntu linux-armv7l(32)
INFO |settings.c:0860:settings_load_ovl| Load settings from /teddycloud/config/config.overlay.ini
INFO |settings.c:0860:settings_load_ovl| Load settings from /teddycloud/config/config.ini
INFO |tls_adapter.c:0204:read_certificate| File '/teddycloud/certs/server/ca-root.pem' assumed PEM style
INFO |tls_adapter.c:0201:read_certificate| File '/teddycloud/certs/server/ca-key.pem' detected as DER style RSA PRIVATE KEY
INFO |tls_adapter.c:0204:read_certificate| File '/teddycloud/certs/server/teddy-cert.pem' assumed PEM style
INFO |tls_adapter.c:0201:read_certificate| File '/teddycloud/certs/server/teddy-key.pem' detected as DER style RSA PRIVATE KEY
INFO |tls_adapter.c:0197:read_certificate| File '/teddycloud/certs/client/ca.der' detected as DER style CERTIFICATE
INFO |tls_adapter.c:0197:read_certificate| File '/teddycloud/certs/client/client.der' detected as DER style CERTIFICATE
INFO |tls_adapter.c:0201:read_certificate| File '/teddycloud/certs/client/private.der' detected as DER style RSA PRIVATE KEY
INFO |settings.c:0860:settings_load_ovl| Load settings from /teddycloud/config/config.overlay.ini
INFO |tls_adapter.c:0390:tls_adapter_init| Loading certificates...
INFO |tls_adapter.c:0204:read_certificate| File '/teddycloud/certs/server/ca-root.pem' assumed PEM style
INFO |tls_adapter.c:0201:read_certificate| File '/teddycloud/certs/server/ca-key.pem' detected as DER style RSA PRIVATE KEY
INFO |tls_adapter.c:0204:read_certificate| File '/teddycloud/certs/server/teddy-cert.pem' assumed PEM style
INFO |tls_adapter.c:0201:read_certificate| File '/teddycloud/certs/server/teddy-key.pem' detected as DER style RSA PRIVATE KEY
INFO |tls_adapter.c:0197:read_certificate| File '/teddycloud/certs/client/ca.der' detected as DER style CERTIFICATE
INFO |tls_adapter.c:0197:read_certificate| File '/teddycloud/certs/client/client.der' detected as DER style CERTIFICATE
INFO |tls_adapter.c:0201:read_certificate| File '/teddycloud/certs/client/private.der' detected as DER style RSA PRIVATE KEY
INFO |toniesJson.c:0280:tonies_readJson| Trying to read /teddycloud/config/tonies.custom.json with size 2
INFO |toniesJson.c:0280:tonies_readJson| Trying to read /teddycloud/config/tonies.json with size 5250327
INFO |toniesJson.c:0100:tonies_update| Updating tonies.json from api.revvox.de...
INFO |cloud_request.c:0200:web_request| Connecting to HTTP server api.revvox.de:443...
INFO |cloud_request.c:0252:web_request| trying IP: 157.90.183.226
INFO |cloud_request.c:0389:web_request| Redirecting to: https://raw.githubusercontent.com/toniebox-reverse-engineering/tonies-json/release/tonies.json
INFO |cloud_request.c:0200:web_request| Connecting to HTTP server raw.githubusercontent.com:443...
INFO |cloud_request.c:0252:web_request| trying IP: 185.199.110.133
INFO |toniesJson.c:0124:tonies_update| ... success updating tonies.json from api.revvox.de, reloading
INFO |toniesJson.c:0280:tonies_readJson| Trying to read /teddycloud/config/tonies.custom.json with size 2
INFO |toniesJson.c:0280:tonies_readJson| Trying to read /teddycloud/config/tonies.json with size 5250559
INFO |toniesJson.c:0211:tonieboxes_update| Updating tonies.json from api.revvox.de...
INFO |cloud_request.c:0200:web_request| Connecting to HTTP server api.revvox.de:443...
INFO |cloud_request.c:0252:web_request| trying IP: 157.90.183.226
INFO |cloud_request.c:0389:web_request| Redirecting to: https://raw.githubusercontent.com/toniebox-reverse-engineering/tonies-json/release/tonieboxes.json
INFO |cloud_request.c:0200:web_request| Connecting to HTTP server raw.githubusercontent.com:443...
INFO |cloud_request.c:0252:web_request| trying IP: 185.199.110.133
INFO |toniesJson.c:0238:tonieboxes_update| ... success updating tonieboxes.json from api.revvox.de, reloading
INFO |toniesJson.c:0280:tonies_readJson| Trying to read /teddycloud/config/tonies.custom.json with size 2
INFO |toniesJson.c:0280:tonies_readJson| Trying to read /teddycloud/config/tonies.json with size 5250559
INFO |server.c:0931:server_init| 1 open HTTPS Web connections
INFO |server.c:0931:server_init| 0 open HTTPS Web connections
INFO |handler_cloud.c:0041:handleCloudTime| >> respond with current time
INFO |handler_cloud.c:0041:handleCloudTime| >> respond with current time
INFO |mqtt.c:0690:mqtt_init_box| Skipping client 'Toniebox' (cn: 'default')
INFO |mqtt.c:0690:mqtt_init_box| Skipping client 'Toniebox' (cn: 'default')
INFO |cloud_request.c:0200:web_request| Connecting to HTTP server prod.de.tbs.toys:443...
INFO |cloud_request.c:0200:web_request| Connecting to HTTP server prod.de.tbs.toys:443...
INFO |cloud_request.c:0252:web_request| trying IP: 18.156.186.144
INFO |cloud_request.c:0252:web_request| trying IP: 3.69.182.181
INFO |cloud_request.c:0486:web_request| Response: '1746352169'
INFO |cloud_request.c:0486:web_request| Response: '1746352169'
Logs cc3200tool:
cc3200tool % cc3200tool -p /dev/tty.usbserial-BG00Z9SS --reset rts write_file c2.der /cert/c2.der
2025-05-04 13:40:46,264 -- Connecting to target...
2025-05-04 13:40:48,782 -- timed out while waiting for ack
2025-05-04 13:40:49,196 -- Connected, reading version...
2025-05-04 13:40:49,198 -- connected to target
2025-05-04 13:40:49,198 -- Version: CC3x00VersionInfo((0, 4, 1, 2), (0, 0, 0, 0), (0, 0, 0, 0), (0, 0, 0, 0), (16, 0, 0, 0))
2025-05-04 13:40:49,199 -- This is a CC3200 device
2025-05-04 13:40:49,199 -- Switching to NWP bootloader...
2025-05-04 13:40:49,215 -- Switching UART to APPS...
2025-05-04 13:40:49,230 -- Resetting communications ...
2025-05-04 13:40:50,654 -- Uploading rbtl3100s.dll...
2025-05-04 13:40:50,654 -- Reading rbtl3100s.dll from file ***/cc3200tool/.venv/lib/python3.12/site-packages/cc3200tool/dll/rbtl3100s.dll
2025-05-04 13:40:50,656 -- Getting storage list...
2025-05-04 13:40:51,405 -- APPS version: CC3x00VersionInfo((0, 4, 0, 2), (0, 0, 0, 0), (0, 0, 0, 0), (0, 0, 0, 0), (16, 0, 0, 0))
2025-05-04 13:40:51,421 -- File exists on target, erasing
2025-05-04 13:40:51,437 -- Erasing file /cert/c2.der...
2025-05-04 13:40:51,549 -- Uploading file c2.der -> /cert/c2.der [1419, disk=1419]...
.
2025-05-04 13:40:51,773 -- Read file after writing for verification...
2025-05-04 13:40:51,789 -- Reading file /cert/c2.der -> /var/folders/wg/l7g30n5s6818j3vhfmhdj0xh0000gn/T/tmp8_xdvltg
2025-05-04 13:40:51,869 -- File /cert/c2.der verified
2025-05-04 13:40:51,869 -- Getting storage info...
2025-05-04 13:40:51,885 -- storage #2 info bytes: 0x10, 0x0, 0x4, 0x0, 0x0, 0x0, 0x0, 0x0
2025-05-04 13:40:51,885 -- Getting storage list...
2025-05-04 13:40:51,904 -- Reading raw storage #2 start 0x0, size 0x2000...
..
2025-05-04 13:40:52,031 -- [1] detected a valid FAT revision: 65
2025-05-04 13:40:52,031 -- Getting storage list...
2025-05-04 13:40:52,050 -- Reading raw storage #2 start 0x1774, size 0x2774...
...
2025-05-04 13:40:52,216 -- selected FAT revision: 65 (active)
2025-05-04 13:40:52,216 -- FAT r65, num files: 27, used/free blocks: 933/91
2025-05-04 13:40:52,216 -- All commands done, bye.