Hi Jason,

It seems like there is a configuration issue. Could you please make sure to
follow below steps to ensure the configs are in order.

Once you create the new keys you can follow [1] to configure it. If you
have created a new hostname in the process of generating the new keys then
you might need to follow [2] as well.

In addition to above, if you have changed the IP and the keys then you
might need to check below configs as well.

1) If you have changed the alias of the default cert from wso2carbon then
make sure to enter the new values to the files listed in [1]. In addition,
make sure to change the "wso2carbon" alias to the new alias in the below
files.

core/repository/deployment/server/jaggeryapps/portal/configs/designer.json
(identityAlias)
core/repository/deployment/server/jaggeryapps/devicemgt/app/conf/app-conf.json
(identityAlias)
core/repository/conf/etc/webapp-authenticator-config.xml (there would be 3
entries)

2) wso2 IoT server uses JWT token for the server to server communication.
If you have changed the cert then could it be possible to update the
identity provider(IDP) with the new cert?. please follow below steps to
update the IDP.

2.1) export the public cert to pem format (if it is not already in the pem
format)

openssl x509 -inform DER -outform PEM -in mycert.cert -out server.crt.pem

2.2) Open server.crt.pem and copy the content between BEGIN CERTIFICATE and
END CERTIFICATE and replace the <Certificate> element in the file based
IDP, which can be found in "core/repository/conf/
identity/identity-providers/iot_default.xml"

3) replace localhost for below entries in core/bin/wso2server.sh

-Diot.keymanager.host="wso2.exterminator.com" \

-Diot.gateway.host="wso2.exterminator.com" \

-Diot.core.host="wso2.exterminator.com" \

4) Set "true" to "EnabledUpdateApi"  in the file -
"core/repository/conf/etc/webapp-publisher-config.xml". This will republish
all the APIs with the new host.

5) In the 
"core/repository/deployment/server/jaggeryapps/portal/configs/designer.json",
Replace localhost to wso2.prokino.nl in the below json entry.

"host": {
    "hostname": "wso2.prokino.nl",
    "port": "",
    "protocol": ""
  }

[1] https://docs.wso2.com/display/IoTS300/Configuring+Keystores+
in+WSO2+Products

[2] https://docs.wso2.com/display/IoTS300/Configuring+WSO2+IoT+
Server+with+the+IP

*Ayyoob Hamza*
*Senior Software Engineer*
WSO2 Inc.; http://wso2.com
email: ayy...@wso2.com cell: +94 77 1681010 <%2B94%2077%207779495>
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