diff --git a/_integration-test/conftest.py b/_integration-test/conftest.py
index e73a7f286c5..462f7cbd045 100644
--- a/_integration-test/conftest.py
+++ b/_integration-test/conftest.py
@@ -25,7 +25,7 @@ def configure_self_hosted_environment(request):
             "exec",
             "-T",
             "web",
-            "sentry",
+            "sentry-server",
             "createuser",
             "--force-update",
             "--superuser",
diff --git a/_integration-test/test_01_basics.py b/_integration-test/test_01_basics.py
index c72f224fb58..e9dd7293e8f 100644
--- a/_integration-test/test_01_basics.py
+++ b/_integration-test/test_01_basics.py
@@ -160,7 +160,7 @@ def test_memcached_django_cache():
             "exec",
             "-T",
             "web",
-            "sentry",
+            "sentry-server",
             "exec",
         ],
         input=script,
@@ -197,7 +197,7 @@ def test_valkey_sentry_cache():
             "exec",
             "-T",
             "web",
-            "sentry",
+            "sentry-server",
             "exec",
         ],
         input=script,
diff --git a/docker-compose.yml b/docker-compose.yml
index 8bb5ac4e0c8..bf86693fbf5 100644
--- a/docker-compose.yml
+++ b/docker-compose.yml
@@ -570,7 +570,7 @@ services:
       args:
         BASE_IMAGE: sentry-self-hosted-local
     entrypoint: "/entrypoint.sh"
-    command: '"0 0 * * * gosu sentry sentry cleanup --days $SENTRY_EVENT_RETENTION_DAYS"'
+    command: '"0 0 * * * gosu sentry sentry-server cleanup --days $SENTRY_EVENT_RETENTION_DAYS"'
   nginx:
     <<: *restart_policy
     ports:
diff --git a/sentry-admin.sh b/sentry-admin.sh
index a46a7d8774d..24d62caf47a 100755
--- a/sentry-admin.sh
+++ b/sentry-admin.sh
@@ -29,7 +29,8 @@ invocation() {
   $dcr --no-deps -v "$VOLUME_MAPPING" -T -e SENTRY_LOG_LEVEL=CRITICAL web "$@" 2>&1
 }
 
-# Function to modify lines starting with `Usage: sentry` to say `Usage: ./sentry-admin.sh` instead.
+# Function to modify lines starting with `Usage: sentry-server` (or the legacy `Usage: sentry`) to say
+# `Usage: ./sentry-admin.sh` instead.
 rename_sentry_bin_in_help_output() {
   local output="$1"
   local help_prefix="$2"
@@ -40,7 +41,8 @@ rename_sentry_bin_in_help_output() {
   while IFS= read -r line; do
     if [[ $line == "Usage: sentry"* ]] && [ "$usage_seen" = false ]; then
       echo -e "\n\n"
-      echo "${line/sentry/./sentry-admin.sh}"
+      line="${line/#Usage: sentry-server/Usage: sentry}"
+      echo "${line/#Usage: sentry/Usage: ./sentry-admin.sh}"
       echo "$help_prefix"
       usage_seen=true
     else
diff --git a/sentry/config.example.yml b/sentry/config.example.yml
index 07135809a3f..d72debdc633 100644
--- a/sentry/config.example.yml
+++ b/sentry/config.example.yml
@@ -66,7 +66,8 @@ system.internal-url-prefix: 'http://web:9000'
 
 # If this file ever becomes compromised, it's important to generate a new key.
 # Changing this value will result in all current sessions being invalidated.
-# A new key can be generated with `$ sentry config generate-secret-key`
+# A new key can be generated with `sentry-server config generate-secret-key`
+# inside the container, e.g. `docker compose run --rm web config generate-secret-key`
 #
 # If you are using SENTRY_SYSTEM_SECRET_KEY that is being set on your `.env` or `.env.custom` file,
 # you should remove this line below as it won't be used anyway.
diff --git a/sentry/sentry.conf.example.py b/sentry/sentry.conf.example.py
index 8767a683aee..cec37fda6ae 100644
--- a/sentry/sentry.conf.example.py
+++ b/sentry/sentry.conf.example.py
@@ -79,7 +79,8 @@ def get_internal_network():
 #
 # If the key ever becomes compromised, it's important to generate a new key.
 # Changing this value will result in all current sessions being invalidated.
-# A new key can be generated with `$ sentry config generate-secret-key`
+# A new key can be generated with `sentry-server config generate-secret-key`
+# inside the container, e.g. `docker compose run --rm web config generate-secret-key`
 if env("SENTRY_SYSTEM_SECRET_KEY"):
     SENTRY_OPTIONS["system.secret-key"] = env("SENTRY_SYSTEM_SECRET_KEY", "")