diff --git a/CHANGELOG.md b/CHANGELOG.md
index 832f2513e5..3fec1185fe 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 v2.55.0 ([#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), [#221](https://github.com/DEVBOX10/sentry-dotnet/pull/221))
+  - [changelog](https://github.com/getsentry/sentry-cli/blob/master/CHANGELOG.md#2550)
+  - [diff](https://github.com/getsentry/sentry-cli/compare/2.18.1...2.55.0)
 - 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..acb433e3f1 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="'$(SolutionName)' != 'Sentry.Unity'">
-    <SentryCLIVersion>2.19.2</SentryCLIVersion>
+    <SentryCLIVersion>2.55.0</SentryCLIVersion>
     <SentryCLIDirectory>$(MSBuildThisFileDirectory)tools\sentry-cli\$(SentryCLIVersion)\</SentryCLIDirectory>
   </PropertyGroup>
 
diff --git a/src/Sentry/Sentry.csproj b/src/Sentry/Sentry.csproj
index 2636d83497..e73b74667e 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 $(_OSArchitecture) == 'Arm64')"
-        Include="sentry-cli-Darwin-arm64" FileHash="a669d9e0df2c7afa1308d05cbc2e78a9b458b0c94f5c111c9e299911bb870308" />
+        Include="sentry-cli-Darwin-arm64" FileHash="93ec099679e6f277710b9b1bf0320df14985693b6ddbfd7fc37500084184bf00" />
       <SentryCLIDownload
         Condition="'$(CI_PUBLISHING_BUILD)' == 'true' Or ($([MSBuild]::IsOSPlatform('OSX')) And $(_OSArchitecture) == 'X64')"
-        Include="sentry-cli-Darwin-x86_64" FileHash="4bd15cb308746d7f1cbed00948c7470bbdb498936f364779defb52b1e27e540b" />
+        Include="sentry-cli-Darwin-x86_64" FileHash="caec00a88edb88b5fb8d860e4d2870a645fc6c9124be858b4e046ce04aa1a5b8" />
       <SentryCLIDownload
         Condition="'$(CI_PUBLISHING_BUILD)' == 'true' Or ($([MSBuild]::IsOSPlatform('Linux')) And $(_OSArchitecture) == 'Arm64')"
-        Include="sentry-cli-Linux-aarch64" FileHash="e8f2153c23bc5b4a44e36981d6b19102e7db78f1472a1d99ea2bdc33a4ee8d7a" />
+        Include="sentry-cli-Linux-aarch64" FileHash="ad6f0669617b82ff78ebe90dac53ea92231d4dda3447f4db9b066424ff3de665" />
       <SentryCLIDownload
         Condition="'$(CI_PUBLISHING_BUILD)' == 'true' Or ($([MSBuild]::IsOSPlatform('Linux')) And $(_OSArchitecture) == 'X86')"
-        Include="sentry-cli-Linux-i686" FileHash="3fe02091eb319242e24f55097404b3b9e767918ab16b4431ad7b3e1ff4b3d14b" />
+        Include="sentry-cli-Linux-i686" FileHash="4017c2d8d756b38f60179d4f481c278265b9be5ca7ae109ee87685b4a16c0cf0" />
       <SentryCLIDownload
         Condition="'$(CI_PUBLISHING_BUILD)' == 'true' Or ($([MSBuild]::IsOSPlatform('Linux')) And $(_OSArchitecture) == 'X64')"
-        Include="sentry-cli-Linux-x86_64" FileHash="12ffbaaa930ea3e5883fd1065b2ecf6167f90f5e4d8ea38925f56ae3eeccc4e7" />
+        Include="sentry-cli-Linux-x86_64" FileHash="28bacd307c8a7b19d54a38e1a8d9808efff7e7382941c68ea6305d1c3385caef" />
       <SentryCLIDownload
         Condition="'$(CI_PUBLISHING_BUILD)' == 'true' Or ($([MSBuild]::IsOSPlatform('Windows')) And $(_OSArchitecture) == 'X86')"
-        Include="sentry-cli-Windows-i686.exe" FileHash="d3879a7adb933978d99c53b28f1d274836e2f6489a3ca642d48358e87fb269b4" />
+        Include="sentry-cli-Windows-i686.exe" FileHash="99dc0674026dcfda3dea0224979099d5feb2fe163998cb0b67ba634ed86eee1e" />
       <SentryCLIDownload
         Condition="'$(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="5f9666720a4d9d018220b46c0ce5e99e2e0377fa0515eda9c5f58113504ca7b3" />
     </ItemGroup>
 
     <!-- Download the files -->