diff --git a/Cargo.lock b/Cargo.lock
index 1127530886..3f096e7b96 100644
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -178,6 +178,7 @@ name = "authentik-common"
 version = "2026.5.0-rc1"
 dependencies = [
  "arc-swap",
+ "authentik-client",
  "aws-lc-rs",
  "axum-server",
  "config",
@@ -189,6 +190,8 @@ dependencies = [
  "nix 0.31.2",
  "notify",
  "pin-project-lite",
+ "reqwest",
+ "reqwest-middleware",
  "rustls",
  "sentry",
  "serde",
@@ -198,6 +201,7 @@ dependencies = [
  "thiserror 2.0.18",
  "time",
  "tokio",
+ "tokio-retry2",
  "tokio-util",
  "tracing",
  "tracing-error",
@@ -3621,6 +3625,16 @@ dependencies = [
  "syn",
 ]
 
+[[package]]
+name = "tokio-retry2"
+version = "0.9.1"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "0266d56e57e6b29becbfce5daa6add8730941ca8192ddd7c24d25bf90c32a743"
+dependencies = [
+ "pin-project",
+ "tokio",
+]
+
 [[package]]
 name = "tokio-rustls"
 version = "0.26.4"
diff --git a/Cargo.toml b/Cargo.toml
index 45f2b4f2be..5ccd2319f0 100644
--- a/Cargo.toml
+++ b/Cargo.toml
@@ -90,6 +90,7 @@ tempfile = "= 3.27.0"
 thiserror = "= 2.0.18"
 time = { version = "= 0.3.47", features = ["macros"] }
 tokio = { version = "= 1.51.1", features = ["full", "tracing"] }
+tokio-retry2 = "= 0.9.1"
 tokio-rustls = "= 0.26.4"
 tokio-util = { version = "= 0.7.18", features = ["full"] }
 tower = "= 0.5.3"
@@ -105,6 +106,7 @@ tracing-subscriber = { version = "= 0.3.23", features = [
 url = "= 2.5.8"
 uuid = { version = "= 1.23.0", features = ["serde", "v4"] }
 
+ak-client = { package = "authentik-client", version = "2026.5.0-rc1", path = "./packages/client-rust" }
 ak-common = { package = "authentik-common", version = "2026.5.0-rc1", path = "./packages/ak-common", default-features = false }
 
 [profile.dev.package.backtrace]
diff --git a/packages/ak-common/Cargo.toml b/packages/ak-common/Cargo.toml
index 33e995c320..771356ae8d 100644
--- a/packages/ak-common/Cargo.toml
+++ b/packages/ak-common/Cargo.toml
@@ -15,6 +15,7 @@ core = ["dep:sqlx"]
 proxy = []
 
 [dependencies]
+ak-client.workspace = true
 arc-swap.workspace = true
 aws-lc-rs.workspace = true
 axum-server.workspace = true
@@ -26,6 +27,8 @@ ipnet.workspace = true
 json-subscriber.workspace = true
 notify.workspace = true
 pin-project-lite.workspace = true
+reqwest.workspace = true
+reqwest-middleware.workspace = true
 rustls.workspace = true
 sentry.workspace = true
 serde.workspace = true
@@ -33,6 +36,7 @@ serde_json.workspace = true
 sqlx = { workspace = true, optional = true }
 thiserror.workspace = true
 time.workspace = true
+tokio-retry2.workspace = true
 tokio-util.workspace = true
 tokio.workspace = true
 tracing-error.workspace = true
diff --git a/packages/ak-common/src/api.rs b/packages/ak-common/src/api.rs
new file mode 100644
index 0000000000..0bd9fcb783
--- /dev/null
+++ b/packages/ak-common/src/api.rs
@@ -0,0 +1,193 @@
+//! Utilities for working with the authentik API client.
+
+use ak_client::apis::configuration::Configuration;
+use eyre::{Result, eyre};
+use url::Url;
+
+use crate::{config, user_agent_outpost};
+
+pub struct ServerConfig {
+    pub host: Url,
+    pub token: String,
+    pub insecure: bool,
+}
+
+impl ServerConfig {
+    pub fn new() -> Result<Self> {
+        let host = config::get()
+            .host
+            .clone()
+            .ok_or_else(|| eyre!("environment variable `AUTHENTIK_HOST` not set"))?;
+        let mut host: Url = host.parse()?;
+        let token = config::get()
+            .token
+            .clone()
+            .ok_or_else(|| eyre!("environment variable `AUTHENTIK_TOKEN` not set"))?;
+        let insecure = config::get().insecure.unwrap_or(false);
+
+        if !host.path().ends_with('/') {
+            host.path_segments_mut()
+                .map_err(|()| eyre!("URL cannot be a base"))?
+                .push("");
+        }
+
+        Ok(Self {
+            host,
+            token,
+            insecure,
+        })
+    }
+}
+
+/// Return a [`Configuration`] object based on external environment variables.
+pub fn make_config() -> Result<Configuration> {
+    let server_config = ServerConfig::new()?;
+
+    let base_path = server_config.host.join("api/v3")?.into();
+
+    let client = reqwest::ClientBuilder::new()
+        .tls_danger_accept_invalid_hostnames(server_config.insecure)
+        .tls_danger_accept_invalid_certs(server_config.insecure)
+        .build()?;
+    let client = reqwest_middleware::ClientBuilder::new(client).build();
+
+    Ok(Configuration {
+        base_path,
+        client,
+        bearer_access_token: Some(server_config.token),
+        user_agent: Some(user_agent_outpost()),
+        ..Default::default()
+    })
+}
+
+#[cfg(test)]
+mod tests {
+    use serde_json::json;
+
+    use super::{ServerConfig, make_config};
+    use crate::config;
+
+    #[test]
+    fn server_config_no_trailing_slash() {
+        config::init().expect("failed to init config");
+        config::set(json!({
+            "host": "http://localhost:9000",
+            "token": "token",
+        }))
+        .expect("failed to set config");
+
+        let server_config = ServerConfig::new().expect("failed to create server config");
+
+        assert_eq!(server_config.host.as_str(), "http://localhost:9000/");
+    }
+
+    #[test]
+    fn server_config_with_trailing_slash() {
+        config::init().expect("failed to init config");
+        config::set(json!({
+            "host": "http://localhost:9000/",
+            "token": "token",
+        }))
+        .expect("failed to set config");
+
+        let server_config = ServerConfig::new().expect("failed to create server config");
+
+        assert_eq!(server_config.host.as_str(), "http://localhost:9000/");
+    }
+
+    #[test]
+    fn server_config_with_path_no_trailing_slash() {
+        config::init().expect("failed to init config");
+        config::set(json!({
+            "host": "http://localhost:9000/authentik",
+            "token": "token",
+        }))
+        .expect("failed to set config");
+
+        let server_config = ServerConfig::new().expect("failed to create server config");
+
+        assert_eq!(
+            server_config.host.as_str(),
+            "http://localhost:9000/authentik/"
+        );
+    }
+
+    #[test]
+    fn server_config_with_path_and_trailing_slash() {
+        config::init().expect("failed to init config");
+        config::set(json!({
+            "host": "http://localhost:9000/authentik/",
+            "token": "token",
+        }))
+        .expect("failed to set config");
+
+        let server_config = ServerConfig::new().expect("failed to create server config");
+
+        assert_eq!(
+            server_config.host.as_str(),
+            "http://localhost:9000/authentik/"
+        );
+    }
+
+    #[test]
+    fn make_config_no_trailing_slash() {
+        config::init().expect("failed to init config");
+        config::set(json!({
+            "host": "http://localhost:9000",
+            "token": "token",
+        }))
+        .expect("failed to set config");
+
+        let api_config = make_config().expect("failed to make config");
+
+        assert_eq!(api_config.base_path, "http://localhost:9000/api/v3");
+    }
+
+    #[test]
+    fn make_config_with_trailing_slash() {
+        config::init().expect("failed to init config");
+        config::set(json!({
+            "host": "http://localhost:9000/",
+            "token": "token",
+        }))
+        .expect("failed to set config");
+
+        let api_config = make_config().expect("failed to make config");
+
+        assert_eq!(api_config.base_path, "http://localhost:9000/api/v3");
+    }
+
+    #[test]
+    fn make_config_with_path_no_trailing_slash() {
+        config::init().expect("failed to init config");
+        config::set(json!({
+            "host": "http://localhost:9000/authentik",
+            "token": "token",
+        }))
+        .expect("failed to set config");
+
+        let api_config = make_config().expect("failed to make config");
+
+        assert_eq!(
+            api_config.base_path,
+            "http://localhost:9000/authentik/api/v3"
+        );
+    }
+
+    #[test]
+    fn make_config_with_path_and_trailing_slash() {
+        config::init().expect("failed to init config");
+        config::set(json!({
+            "host": "http://localhost:9000/authentik/",
+            "token": "token",
+        }))
+        .expect("failed to set config");
+
+        let api_config = make_config().expect("failed to make config");
+
+        assert_eq!(
+            api_config.base_path,
+            "http://localhost:9000/authentik/api/v3"
+        );
+    }
+}
diff --git a/packages/ak-common/src/config/schema.rs b/packages/ak-common/src/config/schema.rs
index 826988782a..896a40e100 100644
--- a/packages/ak-common/src/config/schema.rs
+++ b/packages/ak-common/src/config/schema.rs
@@ -23,6 +23,11 @@ pub struct Config {
     pub web: WebConfig,
 
     pub worker: WorkerConfig,
+
+    // Outpost specific fields
+    pub host: Option<String>,
+    pub token: Option<String>,
+    pub insecure: Option<bool>,
 }
 
 #[derive(Debug, Clone, Serialize, Deserialize)]
diff --git a/packages/ak-common/src/lib.rs b/packages/ak-common/src/lib.rs
index feabf41bac..09d67b87b4 100644
--- a/packages/ak-common/src/lib.rs
+++ b/packages/ak-common/src/lib.rs
@@ -1,5 +1,6 @@
 //! Various utilities used by other crates
 
+pub mod api;
 pub mod arbiter;
 pub use arbiter::{Arbiter, Event, Tasks};
 pub mod config;
@@ -26,6 +27,10 @@ pub fn authentik_full_version() -> String {
     }
 }
 
+pub fn user_agent_outpost() -> String {
+    format!("goauthentik.io/outpost/{}", authentik_full_version())
+}
+
 pub fn authentik_user_agent() -> String {
     format!("authentik@{}", authentik_full_version())
 }
diff --git a/packages/ak-common/src/tracing.rs b/packages/ak-common/src/tracing.rs
index 3902dee2ea..4f51b254ac 100644
--- a/packages/ak-common/src/tracing.rs
+++ b/packages/ak-common/src/tracing.rs
@@ -128,33 +128,91 @@ mod json {
 
 /// Utilities for Sentry
 pub mod sentry {
-    use std::str::FromStr as _;
+    use std::{str::FromStr as _, time::Duration};
 
-    use tracing::trace;
+    use ak_client::apis::root_api::root_config_retrieve;
+    use eyre::{Error, Result};
+    use tokio_retry2::{Retry, RetryError, strategy::FixedInterval};
+    use tracing::{error, trace};
 
-    use crate::{VERSION, authentik_user_agent, config};
+    use crate::{
+        Mode, VERSION, api, authentik_user_agent,
+        config::{self, schema::ErrorReportingConfig},
+    };
+
+    fn get_config() -> Result<ErrorReportingConfig> {
+        // In non-core mode, we are running an outpost and need to grab the error reporting
+        // configuration from the API.
+        if Mode::is_core() {
+            return Ok(config::get().error_reporting.clone());
+        }
+
+        let api_config = api::make_config()?;
+
+        let config = {
+            let retry_strategy = FixedInterval::new(Duration::from_secs(3));
+            let retrieve_config = async || {
+                root_config_retrieve(&api_config)
+                    .await
+                    .map_err(Error::new)
+                    .map_err(RetryError::transient)
+            };
+            let retry_notify = |err: &Error, _duration| {
+                error!(
+                    ?err,
+                    "Failed to fetch configuration from API, retrying in 3 seconds"
+                );
+            };
+            tokio::runtime::Builder::new_current_thread()
+                .enable_all()
+                .build()?
+                .block_on(Retry::spawn_notify(
+                    retry_strategy,
+                    retrieve_config,
+                    retry_notify,
+                ))?
+        };
+
+        let config = config.error_reporting;
+
+        Ok(ErrorReportingConfig {
+            enabled: config.enabled,
+            sentry_dsn: Some(config.sentry_dsn),
+            environment: config.environment,
+            send_pii: config.send_pii,
+            #[expect(
+                clippy::cast_possible_truncation,
+                reason = "This is fine, we'll never get big values here."
+            )]
+            #[expect(
+                clippy::as_conversions,
+                reason = "This is fine, we'll never get big values here."
+            )]
+            sample_rate: config.traces_sample_rate as f32,
+        })
+    }
 
     /// Install the sentry client. This must happen before [`super::install`] is called.
-    pub fn install() -> sentry::ClientInitGuard {
+    pub fn install() -> Result<Option<sentry::ClientInitGuard>> {
+        let config = get_config()?;
+        if !config.enabled {
+            return Ok(None);
+        }
         trace!("setting up sentry");
-        let config = config::get();
-        sentry::init(sentry::ClientOptions {
-            dsn: config.error_reporting.sentry_dsn.clone().map(|dsn| {
+        let debug = config::get().debug;
+        Ok(Some(sentry::init(sentry::ClientOptions {
+            dsn: config.sentry_dsn.clone().map(|dsn| {
                 sentry::types::Dsn::from_str(&dsn).expect("Failed to create sentry DSN")
             }),
             release: Some(format!("authentik@{VERSION}").into()),
-            environment: Some(config.error_reporting.environment.clone().into()),
+            environment: Some(config.environment.clone().into()),
             attach_stacktrace: true,
-            send_default_pii: config.error_reporting.send_pii,
-            sample_rate: config.error_reporting.sample_rate,
-            traces_sample_rate: if config.debug {
-                1.0
-            } else {
-                config.error_reporting.sample_rate
-            },
+            send_default_pii: config.send_pii,
+            sample_rate: config.sample_rate,
+            traces_sample_rate: if debug { 1.0 } else { config.sample_rate },
             user_agent: authentik_user_agent().into(),
             ..sentry::ClientOptions::default()
-        })
+        })))
     }
 }