diff --git a/src/constants.ts b/src/constants.ts
index 2381292fd..81ed06176 100644
--- a/src/constants.ts
+++ b/src/constants.ts
@@ -49,3 +49,9 @@ export const DAY_MS = HOUR_MS * 24;
 // IMPORTANT: When updating this value, we need to update the string located in `AIClearHistoryReminder` component.
 // Reference: https://github.com/Automattic/studio/blob/3dd5c58cdb7998e458d191e508e8e859177225a9/src/components/ai-clear-history-reminder.tsx#L78
 export const CLEAR_HISTORY_REMINDER_TIME = 2 * HOUR_MS; // In milliseconds
+
+// WP-CLI
+export const WP_CLI_DEFAULT_RESPONSE_TIMEOUT = 5 * 60 * 1000; // 5min
+export const WP_CLI_IMPORT_EXPORT_RESPONSE_TIMEOUT_IN_HRS = 6;
+export const WP_CLI_IMPORT_EXPORT_RESPONSE_TIMEOUT =
+	WP_CLI_IMPORT_EXPORT_RESPONSE_TIMEOUT_IN_HRS * 60 * 60 * 1000; // 6hr
diff --git a/src/hooks/use-import-export.tsx b/src/hooks/use-import-export.tsx
index fa3ca15c8..8ac998499 100644
--- a/src/hooks/use-import-export.tsx
+++ b/src/hooks/use-import-export.tsx
@@ -1,6 +1,7 @@
 import * as Sentry from '@sentry/electron/renderer';
-import { __ } from '@wordpress/i18n';
+import { __, sprintf } from '@wordpress/i18n';
 import { createContext, useMemo, useState, useCallback, useContext } from 'react';
+import { WP_CLI_IMPORT_EXPORT_RESPONSE_TIMEOUT_IN_HRS } from 'src/constants';
 import { useIpcListener } from 'src/hooks/use-ipc-listener';
 import { useSiteDetails } from 'src/hooks/use-site-details';
 import { getIpcApi } from 'src/lib/get-ipc-api';
@@ -92,6 +93,18 @@ export const ImportExportProvider = ( { children }: { children: React.ReactNode
 							'The ZIP archive is invalid. Try to unpack and pack it again. If this problem persists, please contact support.'
 						),
 					} );
+				} else if (
+					( error as Error ).message.includes( 'WP-CLI command was canceled (timed out)' )
+				) {
+					await getIpcApi().showErrorMessageBox( {
+						title: __( 'Failed importing site' ),
+						message: sprintf(
+							__(
+								'The import process timed out after %d hours, which can occur when processing very large imports. If the issue persists, please contact support.'
+							),
+							WP_CLI_IMPORT_EXPORT_RESPONSE_TIMEOUT_IN_HRS
+						),
+					} );
 				} else {
 					await getIpcApi().showErrorMessageBox( {
 						title: __( 'Failed importing site' ),
diff --git a/src/lib/import-export/import/importers/importer.ts b/src/lib/import-export/import/importers/importer.ts
index b82ec5d2a..cb0d8c288 100644
--- a/src/lib/import-export/import/importers/importer.ts
+++ b/src/lib/import-export/import/importers/importer.ts
@@ -61,11 +61,11 @@ abstract class BaseImporter extends EventEmitter implements Importer {
 				);
 
 				if ( stderr ) {
-					console.error( `Warning during import of ${ sqlFile }:`, stderr );
+					console.error( `Error during import of ${ sqlFile }:`, stderr );
 				}
 
 				if ( exitCode ) {
-					throw new Error( 'Database import failed' );
+					throw new Error( 'Database import failed: ' + stderr );
 				}
 			} finally {
 				await this.safelyDeletePath( tmpPath );
diff --git a/src/lib/wp-cli-process.ts b/src/lib/wp-cli-process.ts
index 264273284..51eb56578 100644
--- a/src/lib/wp-cli-process.ts
+++ b/src/lib/wp-cli-process.ts
@@ -1,5 +1,9 @@
 import { app, utilityProcess, UtilityProcess } from 'electron';
 import * as Sentry from '@sentry/electron/renderer';
+import {
+	WP_CLI_DEFAULT_RESPONSE_TIMEOUT as DEFAULT_RESPONSE_TIMEOUT,
+	WP_CLI_IMPORT_EXPORT_RESPONSE_TIMEOUT as IMPORT_EXPORT_RESPONSE_TIMEOUT,
+} from 'src/constants';
 import { executeWPCli } from 'vendor/wp-now/src/execute-wp-cli';
 
 // This allows TypeScript to pick up the magic constants that's auto-generated by Forge's Webpack
@@ -11,8 +15,6 @@ export type MessageName = 'execute';
 export type WpCliResult = ReturnType< typeof executeWPCli >;
 export type MessageCanceled = { error: Error; canceled: boolean };
 
-const DEFAULT_RESPONSE_TIMEOUT = 300 * 1000;
-
 export default class WpCliProcess {
 	lastMessageId = 0;
 	process?: UtilityProcess;
@@ -62,7 +64,11 @@ export default class WpCliProcess {
 			args,
 			phpVersion,
 		} );
-		return await this.waitForResponse( message, messageId );
+		const timeout =
+			args[ 0 ] === 'sqlite' && [ 'import', 'export' ].includes( args[ 1 ] )
+				? IMPORT_EXPORT_RESPONSE_TIMEOUT
+				: DEFAULT_RESPONSE_TIMEOUT;
+		return await this.waitForResponse( message, messageId, timeout );
 	}
 
 	async stop() {
diff --git a/src/site-server.ts b/src/site-server.ts
index 973d541a3..c40ce3bb5 100644
--- a/src/site-server.ts
+++ b/src/site-server.ts
@@ -202,11 +202,19 @@ export class SiteServer {
 			return await this.wpCliExecutor.execute( wpCliArgs as string[], { phpVersion } );
 		} catch ( error ) {
 			if ( ( error as MessageCanceled )?.canceled ) {
-				return { stdout: '', stderr: 'wp-cli command canceled', exitCode: 1 };
+				return {
+					stdout: '',
+					stderr: 'WP-CLI command was canceled (timed out)',
+					exitCode: 1,
+				};
 			}
 
 			Sentry.captureException( error );
-			return { stdout: '', stderr: 'error when executing wp-cli command', exitCode: 1 };
+			return {
+				stdout: '',
+				stderr: `Error executing WP-CLI command: ${ ( error as MessageCanceled ).error.message }`,
+				exitCode: 1,
+			};
 		}
 	}