diff --git a/CHANGELOG.md b/CHANGELOG.md
index 19f890cc62..91608d7717 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -12,6 +12,10 @@
 
 - Add `enableAutoConsoleLogs` option to opt out of automatic `console.*` capture while keeping `enableLogs: true` for manual `Sentry.logger.*` calls ([#6235](https://github.com/getsentry/sentry-react-native/pull/6235))
 
+### Fixes
+
+- Resolve `sentry-cli` in isolated dependency layouts ([#6242](https://github.com/getsentry/sentry-react-native/pull/6242))
+
 ### Internal
 
 - Convert `sentry.gradle` to Kotlin DSL (`sentry.gradle.kts`) ([#6119](https://github.com/getsentry/sentry-react-native/pull/6119))
diff --git a/packages/core/scripts/sentry-xcode-debug-files.sh b/packages/core/scripts/sentry-xcode-debug-files.sh
index fe65325aa6..d05f2012c6 100755
--- a/packages/core/scripts/sentry-xcode-debug-files.sh
+++ b/packages/core/scripts/sentry-xcode-debug-files.sh
@@ -32,9 +32,10 @@ RN_PROJECT_ROOT="${SENTRY_PROJECT_ROOT:-${PROJECT_DIR}/..}"
 [ -z "$SOURCEMAP_FILE" ] && export SOURCEMAP_FILE="$DERIVED_FILE_DIR/main.jsbundle.map"
 
 if [ -z "$SENTRY_CLI_EXECUTABLE" ]; then
-  # Try standard resolution safely
+  # Resolve from @sentry/react-native so package managers with isolated dependencies
+  # can find the transitive @sentry/cli dependency.
   RESOLVED_PATH=$(
-    "$LOCAL_NODE_BINARY" --print "require('path').dirname(require.resolve('@sentry/cli/package.json'))" 2>/dev/null
+    "$LOCAL_NODE_BINARY" --print "require('path').dirname(require.resolve('@sentry/cli/package.json', { paths: [require.resolve('@sentry/react-native/package.json')] }))" 2>/dev/null
   ) || true
   if [ -n "$RESOLVED_PATH" ]; then
     SENTRY_CLI_PACKAGE_PATH="$RESOLVED_PATH/bin/sentry-cli"
diff --git a/packages/core/scripts/sentry-xcode.sh b/packages/core/scripts/sentry-xcode.sh
index 229ac90bb2..aa4ead6225 100755
--- a/packages/core/scripts/sentry-xcode.sh
+++ b/packages/core/scripts/sentry-xcode.sh
@@ -27,9 +27,10 @@ if [[ "$SOURCEMAP_FILE" != /* ]]; then
 fi
 
 if [ -z "$SENTRY_CLI_EXECUTABLE" ]; then
-  # Try standard resolution safely
+  # Resolve from @sentry/react-native so package managers with isolated dependencies
+  # can find the transitive @sentry/cli dependency.
   RESOLVED_PATH=$(
-    "$LOCAL_NODE_BINARY" --print "require('path').dirname(require.resolve('@sentry/cli/package.json'))" 2>/dev/null
+    "$LOCAL_NODE_BINARY" --print "require('path').dirname(require.resolve('@sentry/cli/package.json', { paths: [require.resolve('@sentry/react-native/package.json')] }))" 2>/dev/null
   ) || true
   if [ -n "$RESOLVED_PATH" ]; then
     SENTRY_CLI_PACKAGE_PATH="$RESOLVED_PATH/bin/sentry-cli"
diff --git a/packages/core/sentry.gradle.kts b/packages/core/sentry.gradle.kts
index 9c813c7cfb..51163f97a5 100644
--- a/packages/core/sentry.gradle.kts
+++ b/packages/core/sentry.gradle.kts
@@ -167,7 +167,13 @@ fun resolveSentryCliPackagePath(reactRoot: File): String {
     var resolvedCliPath: File? = null
     try {
         val process =
-            ProcessBuilder(listOf("node", "--print", "require.resolve('@sentry/cli/package.json')"))
+            ProcessBuilder(
+                listOf(
+                    "node",
+                    "--print",
+                    "require.resolve('@sentry/cli/package.json', { paths: [require.resolve('@sentry/react-native/package.json')] })",
+                ),
+            )
                 .directory(rootDir)
                 .start()
         val output =
diff --git a/packages/core/test/scripts/sentry-cli-resolution.test.ts b/packages/core/test/scripts/sentry-cli-resolution.test.ts
new file mode 100644
index 0000000000..b77b0174b8
--- /dev/null
+++ b/packages/core/test/scripts/sentry-cli-resolution.test.ts
@@ -0,0 +1,35 @@
+import * as fs from 'fs';
+import * as path from 'path';
+
+const CORE_DIR = path.resolve(__dirname, '../..');
+const EXPO_UPLOAD_SOURCEMAPS_DIR = path.resolve(CORE_DIR, '../expo-upload-sourcemaps');
+const RELATIVE_SENTRY_CLI_RESOLVER =
+  "require.resolve('@sentry/cli/package.json', { paths: [require.resolve('@sentry/react-native/package.json')] })";
+const RELATIVE_EXPO_UPLOAD_SOURCEMAPS_CLI_RESOLVER_PATH =
+  "paths: [require.resolve('@sentry/expo-upload-sourcemaps/package.json')]";
+
+describe('sentry-cli resolution', () => {
+  it('resolves @sentry/cli relative to @sentry/react-native on Android', () => {
+    const gradleScript = fs.readFileSync(path.join(CORE_DIR, 'sentry.gradle.kts'), 'utf8');
+
+    expect(gradleScript).toContain(RELATIVE_SENTRY_CLI_RESOLVER);
+  });
+
+  it('resolves @sentry/cli relative to @sentry/react-native on iOS', () => {
+    const xcodeScript = fs.readFileSync(path.join(CORE_DIR, 'scripts', 'sentry-xcode.sh'), 'utf8');
+    const xcodeDebugFilesScript = fs.readFileSync(
+      path.join(CORE_DIR, 'scripts', 'sentry-xcode-debug-files.sh'),
+      'utf8',
+    );
+
+    expect(xcodeScript).toContain(RELATIVE_SENTRY_CLI_RESOLVER);
+    expect(xcodeDebugFilesScript).toContain(RELATIVE_SENTRY_CLI_RESOLVER);
+  });
+
+  it('resolves @sentry/cli relative to @sentry/expo-upload-sourcemaps in the Expo uploader', () => {
+    const expoUploadSourcemapsScript = fs.readFileSync(path.join(EXPO_UPLOAD_SOURCEMAPS_DIR, 'cli.js'), 'utf8');
+
+    expect(expoUploadSourcemapsScript).toContain("require.resolve('@sentry/cli/bin/sentry-cli'");
+    expect(expoUploadSourcemapsScript).toContain(RELATIVE_EXPO_UPLOAD_SOURCEMAPS_CLI_RESOLVER_PATH);
+  });
+});
diff --git a/packages/expo-upload-sourcemaps/cli.js b/packages/expo-upload-sourcemaps/cli.js
index 98e1057cfb..2a2e6afbd4 100755
--- a/packages/expo-upload-sourcemaps/cli.js
+++ b/packages/expo-upload-sourcemaps/cli.js
@@ -14,6 +14,31 @@ function getEnvVar(varname) {
   return process.env[varname];
 }
 
+function resolveSentryCliBin() {
+  const configuredExecutable = getEnvVar(SENTRY_CLI_EXECUTABLE);
+  if (configuredExecutable) {
+    return configuredExecutable;
+  }
+
+  let dependencyRelativeError;
+  try {
+    return require.resolve('@sentry/cli/bin/sentry-cli', {
+      paths: [require.resolve('@sentry/expo-upload-sourcemaps/package.json')],
+    });
+  } catch (error) {
+    dependencyRelativeError = error;
+  }
+
+  try {
+    return require.resolve('@sentry/cli/bin/sentry-cli');
+  } catch (error) {
+    console.error(`Could not resolve sentry-cli. Set ${SENTRY_CLI_EXECUTABLE} to the sentry-cli executable path.`);
+    console.error('Dependency-relative resolution failed:', dependencyRelativeError);
+    console.error('Standard resolution failed:', error);
+    process.exit(1);
+  }
+}
+
 function getSentryPluginPropertiesFromExpoConfig() {
   try {
     let expoPkgJson;
@@ -187,7 +212,7 @@ let sentryOrg = getEnvVar(SENTRY_ORG);
 let sentryUrl = getEnvVar(SENTRY_URL);
 let sentryProject = getEnvVar(SENTRY_PROJECT);
 let authToken = getEnvVar(SENTRY_AUTH_TOKEN);
-const sentryCliBin = getEnvVar(SENTRY_CLI_EXECUTABLE) || require.resolve('@sentry/cli/bin/sentry-cli');
+const sentryCliBin = resolveSentryCliBin();
 
 if (!sentryOrg || !sentryProject || !sentryUrl) {
   console.log('🐕 Fetching from expo config...');