diff --git a/packages/init/src/lib/setupSentry.ts b/packages/init/src/lib/setupSentry.ts
index c35f7a5df9..578429f224 100644
--- a/packages/init/src/lib/setupSentry.ts
+++ b/packages/init/src/lib/setupSentry.ts
@@ -19,8 +19,8 @@ export function setupSentry(): void {
 		environment: isStableVersion
 			? import.meta.env.MODE || "production"
 			: "alpha",
-		// Increase the default truncation length of 250 to 2500 (x10)
+		// Increase the default truncation length of 250 to 12500 (x50)
 		// to have enough details in Sentry
-		maxValueLength: 2_500,
+		maxValueLength: 12_500,
 	});
 }
diff --git a/packages/init/src/lib/updateSentryContext.ts b/packages/init/src/lib/updateSentryContext.ts
index 1b7a4d028b..55fb8981dc 100644
--- a/packages/init/src/lib/updateSentryContext.ts
+++ b/packages/init/src/lib/updateSentryContext.ts
@@ -39,4 +39,9 @@ export async function updateSentryContext({
 	if (framework) {
 		Sentry.setTag("framework", framework);
 	}
+
+	Sentry.setContext("Process", {
+		"Command used": process.argv.join(" "),
+		cwd: process.cwd(),
+	});
 }
diff --git a/packages/manager/src/auth/PrismicAuthManager.ts b/packages/manager/src/auth/PrismicAuthManager.ts
index c06620bffe..cdc6bd55ae 100644
--- a/packages/manager/src/auth/PrismicAuthManager.ts
+++ b/packages/manager/src/auth/PrismicAuthManager.ts
@@ -295,7 +295,9 @@ export class PrismicAuthManager {
 
 				await this._writePersistedAuthState(authState);
 			} else {
-				throw new InternalError("Failed to refresh authentication token.");
+				throw new InternalError("Failed to refresh authentication token.", {
+					cause: text,
+				});
 			}
 		} else {
 			throw new UnauthenticatedError();
@@ -320,9 +322,9 @@ export class PrismicAuthManager {
 				"User-Agent": SLICE_MACHINE_USER_AGENT,
 			},
 		});
-		const json = await res.json();
 
 		if (res.ok) {
+			const json = await res.json();
 			const { value: profile, error } = decode(PrismicUserProfile, json);
 
 			if (error) {
@@ -333,8 +335,12 @@ export class PrismicAuthManager {
 
 			return profile;
 		} else {
+			const text = await res.text();
 			throw new InternalError(
 				"Failed to retrieve profile from the Prismic user service.",
+				{
+					cause: text,
+				},
 			);
 		}
 	}
diff --git a/packages/manager/src/lib/fetchGitHubReleaseBodyForRelease.ts b/packages/manager/src/lib/fetchGitHubReleaseBodyForRelease.ts
index 14383c20bc..2a36675f5e 100644
--- a/packages/manager/src/lib/fetchGitHubReleaseBodyForRelease.ts
+++ b/packages/manager/src/lib/fetchGitHubReleaseBodyForRelease.ts
@@ -45,7 +45,10 @@ const fetchAllGitHubReleases = async (
 
 		return value;
 	} else {
-		throw new Error(`Invalid GitHub Release response.`);
+		const text = await res.text();
+		throw new Error(`Invalid GitHub Release response.`, {
+			cause: text,
+		});
 	}
 };
 
diff --git a/packages/manager/src/lib/installDependencies.ts b/packages/manager/src/lib/installDependencies.ts
index 507126cd81..b239b9f326 100644
--- a/packages/manager/src/lib/installDependencies.ts
+++ b/packages/manager/src/lib/installDependencies.ts
@@ -45,6 +45,12 @@ export const installDependencies = async (
 	if (!command) {
 		throw new Error(
 			"Failed to begin dependency installation (could not parse command)",
+			{
+				cause: {
+					packageManager: args.packageManager,
+					dependencies: args.dependencies,
+				},
+			},
 		);
 	}
 
diff --git a/packages/manager/src/managers/customTypes/CustomTypesManager.ts b/packages/manager/src/managers/customTypes/CustomTypesManager.ts
index 489415a85a..bf3eaf0f03 100644
--- a/packages/manager/src/managers/customTypes/CustomTypesManager.ts
+++ b/packages/manager/src/managers/customTypes/CustomTypesManager.ts
@@ -252,6 +252,9 @@ export class CustomTypesManager extends BaseManager {
 				} else if (error instanceof prismicCustomTypesClient.ForbiddenError) {
 					throw new UnauthorizedError(
 						"You do not have access to push types to this Prismic repository.",
+						{
+							cause: error,
+						},
 					);
 				} else {
 					throw error;
diff --git a/packages/manager/src/managers/prismicRepository/PrismicRepositoryManager.ts b/packages/manager/src/managers/prismicRepository/PrismicRepositoryManager.ts
index d876482828..0dfcda52be 100644
--- a/packages/manager/src/managers/prismicRepository/PrismicRepositoryManager.ts
+++ b/packages/manager/src/managers/prismicRepository/PrismicRepositoryManager.ts
@@ -65,9 +65,9 @@ export class PrismicRepositoryManager extends BaseManager {
 	async readAll(): Promise<PrismicRepository[]> {
 		const url = new URL("./repositories", API_ENDPOINTS.PrismicUser);
 		const res = await this._fetch({ url });
-		const json = await res.json();
 
 		if (res.ok) {
+			const json = await res.json();
 			const { value: repositories, error } = decode(
 				t.array(PrismicRepository),
 				json,
@@ -81,7 +81,8 @@ export class PrismicRepositoryManager extends BaseManager {
 
 			return repositories;
 		} else {
-			throw new Error(`Failed to read repositories`, { cause: json });
+			const text = await res.text();
+			throw new Error(`Failed to read repositories`, { cause: text });
 		}
 	}
 
@@ -413,7 +414,9 @@ export class PrismicRepositoryManager extends BaseManager {
 					const text = await response.text();
 					throw new Error(text);
 				default:
-					throw new Error(`Unexpected status code ${response.status}`);
+					throw new Error(`Unexpected status code ${response.status}`, {
+						cause: await response.text(),
+					});
 			}
 		} catch (err) {
 			console.error("An error happened while pushing your changes");
diff --git a/packages/manager/src/managers/project/ProjectManager.ts b/packages/manager/src/managers/project/ProjectManager.ts
index 8409ed9e16..0168b9bb75 100644
--- a/packages/manager/src/managers/project/ProjectManager.ts
+++ b/packages/manager/src/managers/project/ProjectManager.ts
@@ -173,7 +173,9 @@ export class ProjectManager extends BaseManager {
 
 		if (error) {
 			// TODO: Write a more friendly and useful message.
-			throw new Error(`Invalid config. ${error.errors.join(", ")}`);
+			throw new Error(`Invalid config. ${error.errors.join(", ")}`, {
+				cause: { rawConfig },
+			});
 		}
 
 		// Allow cached config reading using `SliceMachineManager.prototype.getProjectConfig()`.
diff --git a/packages/manager/src/managers/screenshots/ScreenshotsManager.ts b/packages/manager/src/managers/screenshots/ScreenshotsManager.ts
index 25f222eaa1..fb1f2bdcdd 100644
--- a/packages/manager/src/managers/screenshots/ScreenshotsManager.ts
+++ b/packages/manager/src/managers/screenshots/ScreenshotsManager.ts
@@ -140,6 +140,9 @@ export class ScreenshotsManager extends BaseManager {
 			// Response is not JSON
 			throw new Error(
 				`Invalid AWS ACL response from ${awsACLURL}: ${awsACLText}`,
+				{
+					cause: error,
+				},
 			);
 		}
 
@@ -162,12 +165,16 @@ export class ScreenshotsManager extends BaseManager {
 		);
 
 		if (error) {
-			throw new Error(`Invalid AWS ACL response from ${awsACLURL}`);
+			throw new Error(`Invalid AWS ACL response from ${awsACLURL}`, {
+				cause: error,
+			});
 		}
 
 		const errorMessage = awsACL.error || awsACL.message || awsACL.Message;
 		if (errorMessage) {
-			throw new Error(`Failed to create an AWS ACL: ${errorMessage}`);
+			throw new Error(`Failed to create an AWS ACL: ${errorMessage}`, {
+				cause: error,
+			});
 		}
 
 		this._s3ACL = {
@@ -302,8 +309,12 @@ export class ScreenshotsManager extends BaseManager {
 				url: url.toString(),
 			};
 		} else {
+			const text = await res.text();
 			throw new Error(
 				`Unable to upload screenshot with status code: ${res.status}`,
+				{
+					cause: text,
+				},
 			);
 		}
 	}
@@ -319,8 +330,12 @@ export class ScreenshotsManager extends BaseManager {
 			url: new URL("delete-folder", API_ENDPOINTS.AwsAclProvider),
 		});
 		if (!res.ok) {
+			const text = await res.text();
 			throw new Error(
 				`Unable to delete screenshot folder with status code: ${res.status}`,
+				{
+					cause: text,
+				},
 			);
 		}
 	}
diff --git a/packages/start-slicemachine/src/lib/sentryErrorHandlers.ts b/packages/start-slicemachine/src/lib/sentryErrorHandlers.ts
index 778665076a..de3aa9fde0 100644
--- a/packages/start-slicemachine/src/lib/sentryErrorHandlers.ts
+++ b/packages/start-slicemachine/src/lib/sentryErrorHandlers.ts
@@ -9,7 +9,9 @@ export const node = (name: string, error: unknown): void => {
 	if (checkIsSentryEnabled()) {
 		Sentry.withScope(function (scope) {
 			scope.setTransactionName(name);
-			Sentry.captureException(error);
+			Sentry.captureException(error, {
+				...(error instanceof Error ? { extra: { cause: error.cause } } : {}),
+			});
 		});
 	}
 };
diff --git a/packages/start-slicemachine/src/lib/setupSentry.ts b/packages/start-slicemachine/src/lib/setupSentry.ts
index dec6851aba..70cc80f4a7 100644
--- a/packages/start-slicemachine/src/lib/setupSentry.ts
+++ b/packages/start-slicemachine/src/lib/setupSentry.ts
@@ -34,6 +34,9 @@ export const setupSentry = async (
 		environment: isStableVersion
 			? import.meta.env.MODE || "production"
 			: "alpha",
+		// Increase the default truncation length of 250 to 12500 (x50)
+		// to have enough details in Sentry
+		maxValueLength: 12_500,
 	});
 	if (userProfile) {
 		Sentry.setUser({ id: userProfile.shortId });