diff --git a/devservices/commands/down.py b/devservices/commands/down.py
index 64068f6..1fbacee 100644
--- a/devservices/commands/down.py
+++ b/devservices/commands/down.py
@@ -8,6 +8,7 @@
 from argparse import Namespace
 
 from sentry_sdk import capture_exception
+from sentry_sdk import logger as sentry_logger
 
 from devservices.constants import CONFIG_FILE_NAME
 from devservices.constants import DEPENDENCY_CONFIG_VERSION
@@ -116,6 +117,15 @@ def down(args: Namespace) -> None:
         == DependencyType.SUPERVISOR
     ]
 
+    sentry_logger.info(
+        "Stopping service",
+        extra={
+            "service_name": service.name,
+            "exclude_local": exclude_local,
+            "active_modes": list(active_modes),
+        },
+    )
+
     with Status(
         lambda: console.warning(f"Stopping {service.name}"),
     ) as status:
diff --git a/devservices/commands/up.py b/devservices/commands/up.py
index 8221c58..1d101d6 100644
--- a/devservices/commands/up.py
+++ b/devservices/commands/up.py
@@ -8,6 +8,7 @@
 from argparse import Namespace
 
 from sentry_sdk import capture_exception
+from sentry_sdk import logger as sentry_logger
 from sentry_sdk import set_context
 from sentry_sdk import start_span
 
@@ -94,6 +95,16 @@ def up(args: Namespace, existing_status: Status | None = None) -> None:
     mode = args.mode
     exclude_local = getattr(args, "exclude_local", False)
 
+    sentry_logger.info(
+        "Starting service",
+        extra={
+            "service_name": service.name,
+            "mode": mode,
+            "exclude_local": exclude_local,
+            "available_modes": list(modes.keys()),
+        },
+    )
+
     state = State()
 
     with Status(
diff --git a/devservices/main.py b/devservices/main.py
index d59c96f..b20faf1 100644
--- a/devservices/main.py
+++ b/devservices/main.py
@@ -16,6 +16,7 @@
 from sentry_sdk import set_user
 from sentry_sdk import start_transaction
 from sentry_sdk.integrations.argv import ArgvIntegration
+from sentry_sdk.integrations.logging import LoggingIntegration
 from sentry_sdk.types import Event
 from sentry_sdk.types import Hint
 
@@ -79,7 +80,11 @@ def before_send_transaction(event: Event, hint: Hint) -> Event:
         dsn="https://56470da7302c16e83141f62f88e46449@o1.ingest.us.sentry.io/4507946704961536",
         traces_sample_rate=1.0,
         profiles_sample_rate=1.0,
-        integrations=[ArgvIntegration()],
+        integrations=[
+            ArgvIntegration(),
+            LoggingIntegration(sentry_logs_level=logging.DEBUG),
+        ],
+        enable_logs=True,
         environment=sentry_environment,
         before_send=before_send_error,
         before_send_transaction=before_send_transaction,
diff --git a/devservices/utils/dependencies.py b/devservices/utils/dependencies.py
index 6fe0b8d..ef1ce70 100644
--- a/devservices/utils/dependencies.py
+++ b/devservices/utils/dependencies.py
@@ -14,6 +14,7 @@
 from typing import TypeGuard
 
 from sentry_sdk import capture_message
+from sentry_sdk import logger as sentry_logger
 from sentry_sdk import set_context
 
 from devservices.configs.service_config import Dependency
@@ -417,6 +418,16 @@ def install_dependency(dependency: RemoteConfig) -> set[InstalledRemoteDependenc
         dependency.repo_name,
     )
 
+    sentry_logger.info(
+        "Installing dependency",
+        extra={
+            "repo_name": dependency.repo_name,
+            "repo_link": dependency.repo_link,
+            "branch": dependency.branch,
+            "mode": dependency.mode,
+        },
+    )
+
     os.makedirs(DEVSERVICES_DEPENDENCIES_CACHE_DIR, exist_ok=True)
 
     # Ensure that only one process is installing a specific dependency at a time
@@ -498,6 +509,14 @@ def _update_dependency(
     dependency: RemoteConfig,
     dependency_repo_dir: str,
 ) -> None:
+    sentry_logger.info(
+        "Updating dependency",
+        extra={
+            "repo_name": dependency.repo_name,
+            "repo_link": dependency.repo_link,
+            "branch": dependency.branch,
+        },
+    )
     git_config_manager = GitConfigManager(
         dependency_repo_dir,
         DEPENDENCY_GIT_PARTIAL_CLONE_CONFIG_OPTIONS,
@@ -580,6 +599,14 @@ def _checkout_dependency(
     dependency: RemoteConfig,
     dependency_repo_dir: str,
 ) -> None:
+    sentry_logger.info(
+        "Checking out dependency",
+        extra={
+            "repo_name": dependency.repo_name,
+            "repo_link": dependency.repo_link,
+            "branch": dependency.branch,
+        },
+    )
     with tempfile.TemporaryDirectory() as temp_dir:
         try:
             _run_command(
diff --git a/devservices/utils/docker_compose.py b/devservices/utils/docker_compose.py
index d8a26cf..29a64b2 100644
--- a/devservices/utils/docker_compose.py
+++ b/devservices/utils/docker_compose.py
@@ -12,6 +12,7 @@
 from typing import NamedTuple
 
 from packaging import version
+from sentry_sdk import logger as sentry_logger
 
 from devservices.configs.service_config import load_service_config_from_file
 from devservices.constants import CONFIG_FILE_NAME
@@ -306,6 +307,14 @@ def run_cmd(
     console = Console()
     cmd_pretty = shlex.join(cmd)
 
+    sentry_logger.info(
+        "Running docker compose command",
+        extra={
+            "command": cmd_pretty,
+            "max_retries": retries,
+        },
+    )
+
     proc = None
     retries += 1  # initial try
 
diff --git a/requirements.txt b/requirements.txt
index c3ab060..164227b 100644
--- a/requirements.txt
+++ b/requirements.txt
@@ -2,5 +2,5 @@
 pyyaml==6.0.2
 packaging==24.0
 sentry-devenv==1.9.0
-sentry-sdk==2.27.0
+sentry-sdk==2.39.0
 supervisor==4.2.5