diff --git a/CHANGELOG.md b/CHANGELOG.md
index 832f2513e5..dc5d185672 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -17,9 +17,9 @@
 - Bump Cocoa SDK from v8.7.3 to v8.8.0 ([#2427](https://github.com/getsentry/sentry-dotnet/pull/2427), [#2430](https://github.com/getsentry/sentry-dotnet/pull/2430))
   - [changelog](https://github.com/getsentry/sentry-cocoa/blob/main/CHANGELOG.md#880)
   - [diff](https://github.com/getsentry/sentry-cocoa/compare/8.7.3...8.8.0)
-- Bump CLI from v2.18.1 to v2.19.2 ([#2428](https://github.com/getsentry/sentry-dotnet/pull/2428), [#2431](https://github.com/getsentry/sentry-dotnet/pull/2431), [#2451](https://github.com/getsentry/sentry-dotnet/pull/2451))
-  - [changelog](https://github.com/getsentry/sentry-cli/blob/master/CHANGELOG.md#2192)
-  - [diff](https://github.com/getsentry/sentry-cli/compare/2.18.1...2.19.2)
+- Bump CLI from v2.18.1 to v3.4.2 ([#2428](https://github.com/getsentry/sentry-dotnet/pull/2428), [#2431](https://github.com/getsentry/sentry-dotnet/pull/2431), [#2451](https://github.com/getsentry/sentry-dotnet/pull/2451), [#291](https://github.com/DEVBOX10/sentry-dotnet/pull/291))
+  - [changelog](https://github.com/getsentry/sentry-cli/blob/master/CHANGELOG.md#342)
+  - [diff](https://github.com/getsentry/sentry-cli/compare/2.18.1...3.4.2)
 - Bump Java SDK from v6.22.0 to v6.24.0 ([#2429](https://github.com/getsentry/sentry-dotnet/pull/2429), [#2440](https://github.com/getsentry/sentry-dotnet/pull/2440))
   - [changelog](https://github.com/getsentry/sentry-java/blob/main/CHANGELOG.md#6240)
   - [diff](https://github.com/getsentry/sentry-java/compare/6.22.0...6.24.0)
diff --git a/Directory.Build.props b/Directory.Build.props
index ea2438a99f..55f69a78b2 100644
--- a/Directory.Build.props
+++ b/Directory.Build.props
@@ -100,7 +100,7 @@
 
   <!-- Set the version and local path for Sentry CLI (downloaded in the restore phase of Sentry.csproj) -->
   <PropertyGroup Condition="'$(SolutionName)' != 'Sentry.Unity'">
-    <SentryCLIVersion>2.19.2</SentryCLIVersion>
+    <SentryCLIVersion>3.4.2</SentryCLIVersion>
     <SentryCLIDirectory>$(MSBuildThisFileDirectory)tools\sentry-cli\$(SentryCLIVersion)\</SentryCLIDirectory>
   </PropertyGroup>
 
diff --git a/src/Sentry/Sentry.csproj b/src/Sentry/Sentry.csproj
index 2636d83497..f13923030e 100644
--- a/src/Sentry/Sentry.csproj
+++ b/src/Sentry/Sentry.csproj
@@ -96,25 +96,25 @@
     <ItemGroup>
       <SentryCLIDownload
         Condition="'$(CI_PUBLISHING_BUILD)' == 'true' Or ($([MSBuild]::IsOSPlatform('OSX')) And $(_OSArchitecture) == 'Arm64')"
-        Include="sentry-cli-Darwin-arm64" FileHash="a669d9e0df2c7afa1308d05cbc2e78a9b458b0c94f5c111c9e299911bb870308" />
+        Include="sentry-cli-Darwin-arm64" FileHash="206ff3bdabf40a95ea3a330b8c842d90492dba8033ee6473e5287f74dd03b903" />
       <SentryCLIDownload
         Condition="'$(CI_PUBLISHING_BUILD)' == 'true' Or ($([MSBuild]::IsOSPlatform('OSX')) And $(_OSArchitecture) == 'X64')"
-        Include="sentry-cli-Darwin-x86_64" FileHash="4bd15cb308746d7f1cbed00948c7470bbdb498936f364779defb52b1e27e540b" />
+        Include="sentry-cli-Darwin-x86_64" FileHash="240d9822c8bf6e3f2c893a9d98deb06a7df385531111a1586fc8a2ba8d687f78" />
       <SentryCLIDownload
         Condition="'$(CI_PUBLISHING_BUILD)' == 'true' Or ($([MSBuild]::IsOSPlatform('Linux')) And $(_OSArchitecture) == 'Arm64')"
-        Include="sentry-cli-Linux-aarch64" FileHash="e8f2153c23bc5b4a44e36981d6b19102e7db78f1472a1d99ea2bdc33a4ee8d7a" />
+        Include="sentry-cli-Linux-aarch64" FileHash="6ccc3b59fae821b54da4a35be12a8893b6a25ba1c0c42f78e275ec57018af3d0" />
       <SentryCLIDownload
         Condition="'$(CI_PUBLISHING_BUILD)' == 'true' Or ($([MSBuild]::IsOSPlatform('Linux')) And $(_OSArchitecture) == 'X86')"
-        Include="sentry-cli-Linux-i686" FileHash="3fe02091eb319242e24f55097404b3b9e767918ab16b4431ad7b3e1ff4b3d14b" />
+        Include="sentry-cli-Linux-i686" FileHash="f0d81697f7af7a51d6ddc361f8ceefe109cd9150b70491f7b6fa5ddba66ad7e2" />
       <SentryCLIDownload
         Condition="'$(CI_PUBLISHING_BUILD)' == 'true' Or ($([MSBuild]::IsOSPlatform('Linux')) And $(_OSArchitecture) == 'X64')"
-        Include="sentry-cli-Linux-x86_64" FileHash="12ffbaaa930ea3e5883fd1065b2ecf6167f90f5e4d8ea38925f56ae3eeccc4e7" />
+        Include="sentry-cli-Linux-x86_64" FileHash="d0718d487f2e408ef7d6689c9ee6e9010cd7e842874641156c932f39857f135d" />
       <SentryCLIDownload
         Condition="'$(CI_PUBLISHING_BUILD)' == 'true' Or ($([MSBuild]::IsOSPlatform('Windows')) And $(_OSArchitecture) == 'X86')"
-        Include="sentry-cli-Windows-i686.exe" FileHash="d3879a7adb933978d99c53b28f1d274836e2f6489a3ca642d48358e87fb269b4" />
+        Include="sentry-cli-Windows-i686.exe" FileHash="73183ea067a445578b536890cc08b072f2260f3e52a72890f2492f991b67de63" />
       <SentryCLIDownload
         Condition="'$(CI_PUBLISHING_BUILD)' == 'true' Or ($([MSBuild]::IsOSPlatform('Windows')) And $(_OSArchitecture) != 'X86')"
-        Include="sentry-cli-Windows-x86_64.exe" FileHash="046a8bdf70a02b23820d0fa197d7638b57f31dcc8dedc95e3ffdaf3541fe34cb" />
+        Include="sentry-cli-Windows-x86_64.exe" FileHash="572b4a6c04504302a46e2e1c196ec31cda266b574b1444605426aa8e41d46b8c" />
     </ItemGroup>
 
     <!-- Download the files -->