diff --git a/Cargo.lock b/Cargo.lock
index 53d38efdf..e5af57582 100644
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -1751,7 +1751,7 @@ source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "976dd42dc7e85965fe702eb8164f21f450704bdde31faefd6471dba214cb594e"
 dependencies = [
  "libc",
- "windows-sys 0.52.0",
+ "windows-sys 0.59.0",
 ]
 
 [[package]]
@@ -3047,7 +3047,7 @@ source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "fc2f4eb4bc735547cfed7c0a4922cbd04a4655978c09b54f1f7b228750664c34"
 dependencies = [
  "cfg-if",
- "windows-targets 0.48.5",
+ "windows-targets 0.52.6",
 ]
 
 [[package]]
@@ -4108,7 +4108,7 @@ dependencies = [
  "sha1",
  "sha2",
  "sprintf",
- "thiserror 1.0.69",
+ "thiserror 2.0.12",
  "tokio",
  "tracing",
  "urlencoding",
@@ -4727,7 +4727,7 @@ source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "8a56d757972c98b346a9b766e3f02746cde6dd1cd1d1d563472929fdd74bec4d"
 dependencies = [
  "anyhow",
- "itertools 0.12.1",
+ "itertools 0.14.0",
  "proc-macro2",
  "quote",
  "syn",
@@ -5197,7 +5197,7 @@ dependencies = [
  "errno",
  "libc",
  "linux-raw-sys 0.4.15",
- "windows-sys 0.52.0",
+ "windows-sys 0.59.0",
 ]
 
 [[package]]
@@ -5210,7 +5210,7 @@ dependencies = [
  "errno",
  "libc",
  "linux-raw-sys 0.9.4",
- "windows-sys 0.52.0",
+ "windows-sys 0.59.0",
 ]
 
 [[package]]
@@ -5276,7 +5276,7 @@ dependencies = [
  "security-framework",
  "security-framework-sys",
  "webpki-root-certs",
- "windows-sys 0.52.0",
+ "windows-sys 0.59.0",
 ]
 
 [[package]]
@@ -5503,9 +5503,9 @@ checksum = "56e6fa9c48d24d85fb3de5ad847117517440f6beceb7798af16b4a87d616b8d0"
 
 [[package]]
 name = "sentry"
-version = "0.37.0"
+version = "0.42.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "255914a8e53822abd946e2ce8baa41d4cded6b8e938913b7f7b9da5b7ab44335"
+checksum = "989425268ab5c011e06400187eed6c298272f8ef913e49fcadc3fda788b45030"
 dependencies = [
  "httpdate",
  "reqwest",
@@ -5520,21 +5520,20 @@ dependencies = [
 
 [[package]]
 name = "sentry-backtrace"
-version = "0.37.0"
+version = "0.42.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "00293cd332a859961f24fd69258f7e92af736feaeb91020cff84dac4188a4302"
+checksum = "68e299dd3f7bcf676875eee852c9941e1d08278a743c32ca528e2debf846a653"
 dependencies = [
  "backtrace",
- "once_cell",
  "regex",
  "sentry-core",
 ]
 
 [[package]]
 name = "sentry-contexts"
-version = "0.37.0"
+version = "0.42.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "961990f9caa76476c481de130ada05614cd7f5aa70fb57c2142f0e09ad3fb2aa"
+checksum = "fac0c5d6892cd4c414492fc957477b620026fb3411fca9fa12774831da561c88"
 dependencies = [
  "hostname",
  "libc",
@@ -5546,22 +5545,22 @@ dependencies = [
 
 [[package]]
 name = "sentry-core"
-version = "0.37.0"
+version = "0.42.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "1a6409d845707d82415c800290a5d63be5e3df3c2e417b0997c60531dfbd35ef"
+checksum = "deaa38b94e70820ff3f1f9db3c8b0aef053b667be130f618e615e0ff2492cbcc"
 dependencies = [
- "once_cell",
- "rand 0.8.5",
+ "rand 0.9.0",
  "sentry-types",
  "serde",
  "serde_json",
+ "url",
 ]
 
 [[package]]
 name = "sentry-panic"
-version = "0.37.0"
+version = "0.42.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "609b1a12340495ce17baeec9e08ff8ed423c337c1a84dffae36a178c783623f3"
+checksum = "2b7a23b13c004873de3ce7db86eb0f59fe4adfc655a31f7bbc17fd10bacc9bfe"
 dependencies = [
  "sentry-backtrace",
  "sentry-core",
@@ -5569,9 +5568,9 @@ dependencies = [
 
 [[package]]
 name = "sentry-tower"
-version = "0.37.0"
+version = "0.42.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "4b98005537e38ee3bc10e7d36e7febe9b8e573d03f2ddd85fcdf05d21f9abd6d"
+checksum = "4a303d0127d95ae928a937dcc0886931d28b4186e7338eea7d5786827b69b002"
 dependencies = [
  "axum",
  "http",
@@ -5584,10 +5583,11 @@ dependencies = [
 
 [[package]]
 name = "sentry-tracing"
-version = "0.37.0"
+version = "0.42.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "49f4e86402d5c50239dc7d8fd3f6d5e048221d5fcb4e026d8d50ab57fe4644cb"
+checksum = "fac841c7050aa73fc2bec8f7d8e9cb1159af0b3095757b99820823f3e54e5080"
 dependencies = [
+ "bitflags",
  "sentry-backtrace",
  "sentry-core",
  "tracing-core",
@@ -5596,16 +5596,16 @@ dependencies = [
 
 [[package]]
 name = "sentry-types"
-version = "0.37.0"
+version = "0.42.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "3d3f117b8755dbede8260952de2aeb029e20f432e72634e8969af34324591631"
+checksum = "e477f4d4db08ddb4ab553717a8d3a511bc9e81dde0c808c680feacbb8105c412"
 dependencies = [
  "debugid",
  "hex",
- "rand 0.8.5",
+ "rand 0.9.0",
  "serde",
  "serde_json",
- "thiserror 1.0.69",
+ "thiserror 2.0.12",
  "time",
  "url",
  "uuid",
@@ -5889,11 +5889,11 @@ dependencies = [
 
 [[package]]
 name = "sprintf"
-version = "0.4.0"
+version = "0.4.2"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "46781e6f401f1557f5b4560284baf7268bd9ca531e9e387120a8695fe5bc1fb1"
+checksum = "78222247fc55e10208ed1ba60f8296390bc67a489bc27a36231765d8d6f60ec5"
 dependencies = [
- "thiserror 1.0.69",
+ "thiserror 2.0.12",
 ]
 
 [[package]]
@@ -6112,7 +6112,7 @@ dependencies = [
  "cfg-if",
  "libc",
  "psm",
- "windows-sys 0.52.0",
+ "windows-sys 0.59.0",
 ]
 
 [[package]]
@@ -6255,7 +6255,7 @@ dependencies = [
  "getrandom 0.3.2",
  "once_cell",
  "rustix 1.0.8",
- "windows-sys 0.52.0",
+ "windows-sys 0.59.0",
 ]
 
 [[package]]
@@ -6287,19 +6287,19 @@ dependencies = [
 
 [[package]]
 name = "thiserror-ext"
-version = "0.2.1"
+version = "0.3.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "ef4323942237f7cc071061f2c5f0db919e6053c2cdf58c6bc974883073429737"
+checksum = "5fb7e61141f4141832ca9aad63c3c90023843f944a1975460abdacc64d03f534"
 dependencies = [
- "thiserror 1.0.69",
+ "thiserror 2.0.12",
  "thiserror-ext-derive",
 ]
 
 [[package]]
 name = "thiserror-ext-derive"
-version = "0.2.1"
+version = "0.3.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "96541747c50e6c73e094737938f4f5dfaf50c48a31adff4197a3e2a481371674"
+checksum = "2b5042dd3b562d1d57711be902006a0003fa2781b81d5b2bec07416be31586ff"
 dependencies = [
  "either",
  "proc-macro2",
@@ -7379,7 +7379,7 @@ version = "0.1.9"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "cf221c93e13a30d793f7645a0e7762c55d169dbb0a49671918a2319d289b10bb"
 dependencies = [
- "windows-sys 0.48.0",
+ "windows-sys 0.59.0",
 ]
 
 [[package]]
diff --git a/Cargo.toml b/Cargo.toml
index 6aa2fcf42..1ec140626 100644
--- a/Cargo.toml
+++ b/Cargo.toml
@@ -572,18 +572,18 @@ features = [
 
 # Sentry error tracking
 [workspace.dependencies.sentry]
-version = "0.37.0"
+version = "0.42.0"
 default-features = false
 features = ["backtrace", "contexts", "panic", "tower", "reqwest"]
 
 # Sentry tower layer
 [workspace.dependencies.sentry-tower]
-version = "0.37.0"
+version = "0.42.0"
 features = ["http", "axum-matched-path"]
 
 # Sentry tracing integration
 [workspace.dependencies.sentry-tracing]
-version = "0.37.0"
+version = "0.42.0"
 
 # Serialization and deserialization
 [workspace.dependencies.serde]
@@ -645,7 +645,7 @@ features = [
 version = "2.0.12"
 
 [workspace.dependencies.thiserror-ext]
-version = "0.2.1"
+version = "0.3.0"
 
 # Async runtime
 [workspace.dependencies.tokio]
diff --git a/crates/cli/src/main.rs b/crates/cli/src/main.rs
index 7cf646564..5df40da83 100644
--- a/crates/cli/src/main.rs
+++ b/crates/cli/src/main.rs
@@ -128,8 +128,6 @@ async fn try_main() -> anyhow::Result<ExitCode> {
             release: Some(VERSION.into()),
             sample_rate: telemetry_config.sentry.sample_rate.unwrap_or(1.0),
             traces_sample_rate: telemetry_config.sentry.traces_sample_rate.unwrap_or(0.0),
-            auto_session_tracking: true,
-            session_mode: sentry::SessionMode::Request,
             ..Default::default()
         },
     ));
diff --git a/crates/cli/src/server.rs b/crates/cli/src/server.rs
index c61c1090f..ec3c2ddd7 100644
--- a/crates/cli/src/server.rs
+++ b/crates/cli/src/server.rs
@@ -333,7 +333,7 @@ pub fn build_router(
         // which is the other way around compared to `tower::ServiceBuilder`.
         // So even if the Sentry docs has an example that does
         // 'NewSentryHttpLayer then SentryHttpLayer', we must do the opposite.
-        .layer(SentryHttpLayer::with_transaction())
+        .layer(SentryHttpLayer::new().enable_transaction())
         .layer(NewSentryLayer::new_from_top())
         .with_state(state)
 }
diff --git a/deny.toml b/deny.toml
index dc5498bbe..a1e598518 100644
--- a/deny.toml
+++ b/deny.toml
@@ -60,7 +60,6 @@ multiple-versions = "deny"
 skip = [
     { name = "regex-syntax", version = "0.6.29" },   # tracing-subscriber[env-filter] -> matchers depends on the old version
     { name = "regex-automata", version = "0.1.10" }, # ^
-    { name = "itertools", version = "0.12.1" },      # otel -> prost depends on this old version
     { name = "itertools", version = "0.13.0" },      # zxcvbn depends on this old version
     { name = "indexmap", version = "1.9.3" },        # schemars depends on this old version
     { name = "hashbrown", version = "0.12.3" },      # schemars -> indexmap depends on this old version