diff --git a/x-pack/plugins/reporting/server/config/index.ts b/x-pack/plugins/reporting/server/config/index.ts
index 963895d1fe583..2d1e40b30935b 100644
--- a/x-pack/plugins/reporting/server/config/index.ts
+++ b/x-pack/plugins/reporting/server/config/index.ts
@@ -30,38 +30,32 @@ export const config: PluginConfigDescriptor<ReportingConfigType> = {
           configPath: `${fromPath}.roles.enabled`,
           level: 'warning',
           title: i18n.translate('xpack.reporting.deprecations.reportingRoles.title', {
-            defaultMessage: 'Setting "{fromPath}.roles" is deprecated',
+            defaultMessage: 'The [{fromPath}.roles] setting is deprecated',
             values: { fromPath },
           }),
           // TODO: once scheduled reports is released, restate this to say that we have no access to scheduled reporting.
           // https://github.com/elastic/kibana/issues/79905
           message: i18n.translate('xpack.reporting.deprecations.reportingRoles.description', {
             defaultMessage:
-              `Use Kibana application privileges to grant reporting privileges.` +
-              ` Using  "{fromPath}.roles.allow" to grant reporting privileges` +
-              ` is deprecated.` +
-              ` The "{fromPath}.roles.enabled" setting will default to false` +
-              ` in a future release.`,
-            values: { fromPath },
+              `The default mechanism for Reporting privilege will work differently in future versions,` +
+              ` which will affect the behavior of this cluster. Set [xpack.reporting.roles.enabled] to` +
+              ` [false] to adopt the future behavior before upgrading.`,
           }),
           correctiveActions: {
             manualSteps: [
               i18n.translate('xpack.reporting.deprecations.reportingRoles.manualStepOne', {
-                defaultMessage: `Set "xpack.reporting.roles.enabled" to "false" in kibana.yml.`,
-              }),
-              i18n.translate('xpack.reporting.deprecations.reportingRoles.manualStepOnePartOne', {
-                defaultMessage: `Remove "xpack.reporting.roles.allow" to "false" in kibana.yml, if present.`,
+                defaultMessage: `Set [xpack.reporting.roles.enabled] to [false] in kibana.yml.`,
               }),
               i18n.translate('xpack.reporting.deprecations.reportingRoles.manualStepTwo', {
+                defaultMessage: `Remove [xpack.reporting.roles.allow] in kibana.yml, if present.`,
+              }),
+              i18n.translate('xpack.reporting.deprecations.reportingRoles.manualStepThree', {
                 defaultMessage:
                   `Create one or more roles that grant the Kibana application` +
                   ` privilege for reporting from **Management > Security > Roles**.`,
               }),
-              i18n.translate('xpack.reporting.deprecations.reportingRoles.manualStepThree', {
-                defaultMessage:
-                  `Grant reporting privileges to users by assigning one of the new roles.` +
-                  ` Users assigned a reporting role specified in "xpack.reporting.roles.allow"` +
-                  ` will no longer have reporting privileges, they must be assigned an application privilege based role.`,
+              i18n.translate('xpack.reporting.deprecations.reportingRoles.manualStepFour', {
+                defaultMessage: `Grant reporting privileges to users by assigning one of the new roles.`,
               }),
             ],
           },
diff --git a/x-pack/plugins/reporting/server/deprecations/reporting_role.ts b/x-pack/plugins/reporting/server/deprecations/reporting_role.ts
index 355a83c13a37e..180c3afdf9b39 100644
--- a/x-pack/plugins/reporting/server/deprecations/reporting_role.ts
+++ b/x-pack/plugins/reporting/server/deprecations/reporting_role.ts
@@ -57,32 +57,39 @@ async function getUsersDeprecations(
 ): Promise<DeprecationsDetails[]> {
   const usingDeprecatedConfig = !reportingCore.getContract().usesUiCapabilities();
   const strings = {
-    title: i18n.translate('xpack.reporting.deprecations.reportingRoleUsersTitle', {
+    title: i18n.translate('xpack.reporting.deprecations.reportingRoleUsers.title', {
       defaultMessage: 'The "{reportingUserRoleName}" role is deprecated: check user roles',
       values: { reportingUserRoleName: REPORTING_USER_ROLE_NAME },
     }),
-    message: i18n.translate('xpack.reporting.deprecations.reportingRoleUsersMessage', {
+    message: i18n.translate('xpack.reporting.deprecations.reportingRoleUsers.description', {
       defaultMessage:
-        'Existing users have their Reporting privilege granted by a deprecated setting.',
+        `The default mechanism for Reporting privilege will work differently in future versions, and` +
+        ` this cluster contains users who have a deprecated role for this privilege.` +
+        ` Set [xpack.reporting.roles.enabled] to [false] to adopt the future behavior before upgrading.`,
     }),
     manualSteps: (usersRoles: string) => [
       ...(usingDeprecatedConfig
         ? [
             i18n.translate('xpack.reporting.deprecations.reportingRoleUsers.manualStepOne', {
-              defaultMessage: 'Set "xpack.reporting.roles.enabled: false" in kibana.yml.',
+              defaultMessage: 'Set [xpack.reporting.roles.enabled] to [false] in kibana.yml.',
             }),
             i18n.translate('xpack.reporting.deprecations.reportingRoleUsers.manualStepTwo', {
-              defaultMessage: 'Remove "xpack.reporting.roles.allow" in kibana.yml, if present.',
+              defaultMessage: 'Remove [xpack.reporting.roles.allow] in kibana.yml, if present.',
             }),
           ]
         : []),
 
       i18n.translate('xpack.reporting.deprecations.reportingRoleUsers.manualStepThree', {
-        defaultMessage: 'Create a custom role with Kibana privileges to grant access to Reporting.',
+        defaultMessage:
+          `Create one or more roles that grant the Kibana application` +
+          ` privilege for reporting from **Management > Security > Roles**.`,
       }),
       i18n.translate('xpack.reporting.deprecations.reportingRoleUsers.manualStepFour', {
+        defaultMessage: `Grant reporting privileges to users by assigning one of the new roles.`,
+      }),
+      i18n.translate('xpack.reporting.deprecations.reportingRoleUsers.manualStepFive', {
         defaultMessage:
-          'Remove the "reporting_user" role from all users and add the custom role. The affected users are: {usersRoles}.',
+          'Remove the "reporting_user" role from all users and add the custom role. The affected users are: [{usersRoles}].',
         values: { usersRoles },
       }),
     ],
@@ -136,18 +143,21 @@ async function getRoleMappingsDeprecations(
 ): Promise<DeprecationsDetails[]> {
   const usingDeprecatedConfig = !reportingCore.getContract().usesUiCapabilities();
   const strings = {
-    title: i18n.translate('xpack.reporting.deprecations.reportingRoleMappingsTitle', {
+    title: i18n.translate('xpack.reporting.deprecations.reportingRoleMappings.title', {
       defaultMessage: 'The "{reportingUserRoleName}" role is deprecated: check role mappings',
       values: { reportingUserRoleName: REPORTING_USER_ROLE_NAME },
     }),
-    message: i18n.translate('xpack.reporting.deprecations.reportingRoleMappingsMessage', {
-      defaultMessage: 'Existing roles are mapped to a deprecated role for Reporting privileges',
+    message: i18n.translate('xpack.reporting.deprecations.reportingRoleMappings.description', {
+      defaultMessage:
+        `The default mechanism for Reporting privilege will work differently in future versions, and` +
+        ` this cluster contains role mappings that are mapped to a deprecated role for this privilege.` +
+        ` Set [xpack.reporting.roles.enabled] to [false] to adopt the future behavior before upgrading.`,
     }),
     manualSteps: (roleMappings: string) => [
       ...(usingDeprecatedConfig
         ? [
             i18n.translate('xpack.reporting.deprecations.reportingRoleMappings.manualStepOne', {
-              defaultMessage: 'Set "xpack.reporting.roles.enabled: false" in kibana.yml.',
+              defaultMessage: `Set [xpack.reporting.roles.enabled] to [false] in kibana.yml.`,
             }),
             i18n.translate('xpack.reporting.deprecations.reportingRoleMappings.manualStepTwo', {
               defaultMessage: 'Remove "xpack.reporting.roles.allow" in kibana.yml, if present.',
@@ -156,11 +166,17 @@ async function getRoleMappingsDeprecations(
         : []),
 
       i18n.translate('xpack.reporting.deprecations.reportingRoleMappings.manualStepThree', {
-        defaultMessage: 'Create a custom role with Kibana privileges to grant access to Reporting.',
+        defaultMessage:
+          `Create one or more roles that grant the Kibana application` +
+          ` privilege for reporting from **Management > Security > Roles**.`,
       }),
       i18n.translate('xpack.reporting.deprecations.reportingRoleMappings.manualStepFour', {
+        defaultMessage: `Grant reporting privileges to users by assigning one of the new roles.`,
+      }),
+      i18n.translate('xpack.reporting.deprecations.reportingRoleMappings.manualStepFive', {
         defaultMessage:
-          'Remove the "reporting_user" role from all role mappings and add the custom role. The affected role mappings are: {roleMappings}.',
+          'Remove the "reporting_user" role from all role mappings and add the custom role.' +
+          ' The affected role mappings are: {roleMappings}.',
         values: { roleMappings },
       }),
     ],