diff --git a/server/package-lock.json b/server/package-lock.json
index dac79faa8..3cb17bea6 100644
--- a/server/package-lock.json
+++ b/server/package-lock.json
@@ -26,6 +26,7 @@
 				"got": "14.4.7",
 				"handlebars": "^4.7.8",
 				"helmet": "^8.0.0",
+				"hpagent": "1.2.0",
 				"isomorphic-dompurify": "^2.26.0",
 				"jmespath": "^0.16.0",
 				"jsdom": "^26.1.0",
@@ -7778,6 +7779,15 @@
 				"node": ">=18.0.0"
 			}
 		},
+		"node_modules/hpagent": {
+			"version": "1.2.0",
+			"resolved": "https://registry.npmjs.org/hpagent/-/hpagent-1.2.0.tgz",
+			"integrity": "sha512-A91dYTeIB6NoXG+PxTQpCCDDnfHsW9kc06Lvpu1TEe9gnd6ZFeiBoRO9JvzEv6xK7EX97/dUE8g/vBMTqTS3CA==",
+			"license": "MIT",
+			"engines": {
+				"node": ">=14"
+			}
+		},
 		"node_modules/html-encoding-sniffer": {
 			"version": "4.0.0",
 			"resolved": "https://registry.npmjs.org/html-encoding-sniffer/-/html-encoding-sniffer-4.0.0.tgz",
diff --git a/server/package.json b/server/package.json
index f0362bb13..5e67192db 100755
--- a/server/package.json
+++ b/server/package.json
@@ -49,6 +49,7 @@
 		"got": "14.4.7",
 		"handlebars": "^4.7.8",
 		"helmet": "^8.0.0",
+		"hpagent": "1.2.0",
 		"isomorphic-dompurify": "^2.26.0",
 		"jmespath": "^0.16.0",
 		"jsdom": "^26.1.0",
diff --git a/server/src/config/services.worker.ts b/server/src/config/services.worker.ts
index b0bdff2d6..9b4ea8609 100644
--- a/server/src/config/services.worker.ts
+++ b/server/src/config/services.worker.ts
@@ -26,7 +26,7 @@ import { NotificationReactor } from "@/worker/reactors/reactor.notification.js";
 import { IncidentReactor } from "@/worker/reactors/reactor.incident.js";
 import { ReactorDispatcher } from "@/worker/reactors/reactor.dispatcher.js";
 import { DBQueueWorker } from "@/worker/worker.db-queue.js";
-
+import { ProxyResolver } from "@/service/network/ProxyResolver.js";
 // Network providers
 import { PingProvider } from "@/service/network/PingProvider.js";
 import { HttpProvider } from "@/service/network/HttpProvider.js";
@@ -64,6 +64,7 @@ export const buildWorker = async (shared: SharedServices, envSettings: EnvConfig
 		incidentsRepository,
 		teamsRepository,
 		maintenanceWindowsRepository,
+		proxiesRepository,
 	} = shared;
 
 	// ***********************
@@ -93,6 +94,7 @@ export const buildWorker = async (shared: SharedServices, envSettings: EnvConfig
 		dnsProvider,
 	]);
 
+	const proxyResolver = new ProxyResolver(proxiesRepository, settingsService, logger);
 	const bufferService = new BufferService(logger, checkService, geoChecksService, settingsService, jobsRepository);
 	const statusService = new StatusService(logger, monitorsRepository, monitorStatsRepository);
 	const monitorStatusPolicy = new MonitorStatusPolicy();
@@ -110,7 +112,15 @@ export const buildWorker = async (shared: SharedServices, envSettings: EnvConfig
 	// Check producer/evaluator
 	// Handles creating and evaluatiog checks
 	// ***********************
-	const checkProducer = new CheckProducer(monitorsRepository, maintenanceWindowsRepository, checkService, networkService, bufferService, logger);
+	const checkProducer = new CheckProducer(
+		monitorsRepository,
+		maintenanceWindowsRepository,
+		checkService,
+		networkService,
+		proxyResolver,
+		bufferService,
+		logger
+	);
 	const checkEvaluator = new CheckEvaluator(statusService, monitorStatusPolicy);
 	const geoCheckPipeline = new GeoChecksPipeline(maintenanceWindowsRepository, geoChecksService, bufferService, logger);
 
diff --git a/server/src/domain/proxies/proxy.repository.interface.ts b/server/src/domain/proxies/proxy.repository.interface.ts
index a235d0df4..5d39ddb80 100644
--- a/server/src/domain/proxies/proxy.repository.interface.ts
+++ b/server/src/domain/proxies/proxy.repository.interface.ts
@@ -5,6 +5,7 @@ export interface IProxiesRepository {
 	create(proxyData: Partial<Proxy>): Promise<Proxy>;
 	// read
 	findById(proxyId: string, teamId: string): Promise<Proxy>;
+	findByIdOrNull(proxyId: string, teamId?: string): Promise<Proxy | null>;
 	findByTeamId(teamId: string): Promise<Proxy[]>;
 	// update
 	updateById(proxyId: string, teamId: string, patch: Partial<Proxy>, options?: { unsetPassword?: boolean; unsetUsername?: boolean }): Promise<Proxy>;
diff --git a/server/src/domain/proxies/proxy.repository.mongo.ts b/server/src/domain/proxies/proxy.repository.mongo.ts
index 3ff810587..454ef68ab 100644
--- a/server/src/domain/proxies/proxy.repository.mongo.ts
+++ b/server/src/domain/proxies/proxy.repository.mongo.ts
@@ -3,7 +3,7 @@ import { Proxy } from "@/domain/proxies/proxy.type.js";
 import { ProxyDocument, ProxyModel } from "@/domain/proxies/proxy.model.js";
 import { AppError } from "@/utils/AppError.js";
 import { toStringId, toDateString } from "@/utils/mongoMappers.js";
-import { UpdateQuery } from "mongoose";
+import { Error as MongooseError, UpdateQuery } from "mongoose";
 
 const SERVICE_NAME = "ProxiesRepository";
 
@@ -45,6 +45,18 @@ class MongoProxiesRepository implements IProxiesRepository {
 		return this.toEntity(proxy);
 	}
 
+	async findByIdOrNull(proxyId: string, teamId?: string): Promise<Proxy | null> {
+		try {
+			const proxy = await ProxyModel.findOne(teamId ? { _id: proxyId, teamId } : { _id: proxyId });
+			return proxy ? this.toEntity(proxy) : null;
+		} catch (error) {
+			if (error instanceof MongooseError.CastError) {
+				return null;
+			}
+			throw error;
+		}
+	}
+
 	async findByTeamId(teamId: string): Promise<Proxy[]> {
 		const proxies = await ProxyModel.find({ teamId });
 		return proxies.map(this.toEntity);
diff --git a/server/src/service/network/HttpProvider.ts b/server/src/service/network/HttpProvider.ts
index fb5f9fea5..1ef35f474 100644
--- a/server/src/service/network/HttpProvider.ts
+++ b/server/src/service/network/HttpProvider.ts
@@ -9,11 +9,17 @@ import { Monitor, MonitorType } from "@/domain/monitors/monitor.type.js";
 import { isStatusUp } from "@/service/network/utils.js";
 import { NETWORK_ERROR } from "@/types/network.js";
 import CacheableLookup from "cacheable-lookup";
+import { HttpProxyAgent, HttpsProxyAgent } from "hpagent";
+import { CheckContext } from "@/types/network.js";
+
+export const PROXY_CONNECT_ERROR_CODES = new Set(["ECONNREFUSED", "ECONNRESET", "EHOSTUNREACH", "ENETUNREACH", "ENOTFOUND", "EAI_AGAIN", "EPIPE"]);
 
 export class HttpProvider implements IStatusProvider<HttpStatusPayload> {
 	readonly type = "http";
 
 	// Shared, pooled agents reused across every check
+	private static readonly PROXY_AGENT_CACHE_MAX = 50;
+	private readonly proxyAgents = new Map<string, { http: HttpProxyAgent; https: HttpsProxyAgent }>();
 	private readonly httpAgent: HttpAgent;
 	private readonly httpsAgent: HttpsAgent;
 	private readonly httpsAgentInsecure: HttpsAgent;
@@ -41,6 +47,44 @@ export class HttpProvider implements IStatusProvider<HttpStatusPayload> {
 		return type === "http";
 	}
 
+	private proxyFailureMessage = (error: RequestError, proxyUrl: string): string | undefined => {
+		if (error.response || !error.code || !PROXY_CONNECT_ERROR_CODES.has(error.code)) {
+			return undefined;
+		}
+		const { hostname, port } = new URL(proxyUrl);
+		return `Proxy connection failed (${hostname}:${port}): ${error.message}`;
+	};
+
+	private getProxyAgents(proxyUrl: string, ignoreTlsErrors: boolean) {
+		const key = `${proxyUrl}|${ignoreTlsErrors}`;
+		const hit = this.proxyAgents.get(key);
+		// Agent already exists, refresh
+		if (hit) {
+			this.proxyAgents.delete(key); // Refresh
+			this.proxyAgents.set(key, hit);
+			return hit;
+		}
+
+		// Create new agents
+		const agentOptions = { keepAlive: true, maxSockets: 256, maxFreeSockets: 256, proxy: proxyUrl };
+		const pair = {
+			http: new HttpProxyAgent(agentOptions),
+			https: new HttpsProxyAgent({ ...agentOptions, rejectUnauthorized: !ignoreTlsErrors }),
+		};
+
+		// Cache agents
+		this.proxyAgents.set(key, pair);
+		if (this.proxyAgents.size > HttpProvider.PROXY_AGENT_CACHE_MAX) {
+			const [oldestKey] = this.proxyAgents.keys(); // Destructuring gets the first inserted, ie oldest, item
+			if (oldestKey === undefined) return pair;
+			const oldest = this.proxyAgents.get(oldestKey);
+			oldest?.http.destroy();
+			oldest?.https.destroy();
+			this.proxyAgents.delete(oldestKey);
+		}
+		return pair;
+	}
+
 	private buildResponse<T>(
 		monitor: Monitor,
 		opts: {
@@ -113,20 +157,22 @@ export class HttpProvider implements IStatusProvider<HttpStatusPayload> {
 		};
 	}
 
-	private handleHttpError<T>(error: unknown, monitor: Monitor): MonitorStatusResponse<T> {
+	private handleHttpError<T>(error: unknown, monitor: Monitor, ctx?: CheckContext): MonitorStatusResponse<T> {
 		if (error instanceof HTTPError || error instanceof RequestError) {
 			const statusCode = error.response?.statusCode;
 			const statusUp = isStatusUp(statusCode, monitor.customUpCodes);
 			const responseTime = error.timings?.phases?.total ?? 0;
 
 			if (!statusUp) {
+				const message = (ctx?.proxyUrl && error instanceof RequestError && this.proxyFailureMessage(error, ctx.proxyUrl)) || error.message;
+
 				return {
 					monitorId: monitor.id,
 					teamId: monitor.teamId,
 					type: monitor.type,
 					status: false,
 					code: statusCode ?? NETWORK_ERROR,
-					message: error.message,
+					message: message,
 					responseTime,
 					timings: error.timings,
 					payload: null as T,
@@ -156,7 +202,7 @@ export class HttpProvider implements IStatusProvider<HttpStatusPayload> {
 		};
 	}
 
-	async handle<T>(monitor: Monitor): Promise<MonitorStatusResponse<T>> {
+	async handle<T>(monitor: Monitor, ctx?: CheckContext): Promise<MonitorStatusResponse<T>> {
 		const { url, secret, ignoreTlsErrors } = monitor;
 
 		if (!url) {
@@ -167,10 +213,12 @@ export class HttpProvider implements IStatusProvider<HttpStatusPayload> {
 			headers: monitor.secret ? { Authorization: `Bearer ${secret}` } : undefined,
 		};
 
-		options.agent = {
-			http: this.httpAgent,
-			https: ignoreTlsErrors ? this.httpsAgentInsecure : this.httpsAgent,
-		};
+		options.agent = ctx?.proxyUrl
+			? this.getProxyAgents(ctx.proxyUrl, Boolean(ignoreTlsErrors))
+			: {
+					http: this.httpAgent,
+					https: ignoreTlsErrors ? this.httpsAgentInsecure : this.httpsAgent,
+				};
 
 		options.method = monitor.method;
 
@@ -188,7 +236,7 @@ export class HttpProvider implements IStatusProvider<HttpStatusPayload> {
 				timings: response.timings,
 			});
 		} catch (error: unknown) {
-			return this.handleHttpError(error, monitor);
+			return this.handleHttpError(error, monitor, ctx);
 		}
 	}
 }
diff --git a/server/src/service/network/IStatusProvider.ts b/server/src/service/network/IStatusProvider.ts
index 6da91b30f..e8f63f671 100644
--- a/server/src/service/network/IStatusProvider.ts
+++ b/server/src/service/network/IStatusProvider.ts
@@ -1,8 +1,8 @@
 import { Monitor, MonitorType } from "@/domain/monitors/monitor.type.js";
 import { MonitorStatusResponse } from "@/types/network.js";
-
+import { CheckContext } from "@/types/network.js";
 export interface IStatusProvider<T> {
 	type: string;
 	supports: (type: MonitorType) => boolean;
-	handle(monitor: Monitor): Promise<MonitorStatusResponse<T>>;
+	handle(monitor: Monitor, ctx?: CheckContext): Promise<MonitorStatusResponse<T>>;
 }
diff --git a/server/src/service/network/ProxyResolver.ts b/server/src/service/network/ProxyResolver.ts
new file mode 100644
index 000000000..573905f4b
--- /dev/null
+++ b/server/src/service/network/ProxyResolver.ts
@@ -0,0 +1,111 @@
+import { ISettingsService } from "@/domain/app-settings/app-settings.service.js";
+import { Monitor } from "@/domain/monitors/monitor.type.js";
+import { IProxiesRepository } from "@/domain/proxies/proxy.repository.interface.js";
+import { ILogger } from "@/utils/logger.js";
+import { Proxy } from "@/domain/proxies/proxy.type.js";
+
+export interface IProxyResolver {
+	resolve(monitor: Monitor): Promise<string | undefined>;
+}
+
+const SERVICE_NAME = "ProxyResolver";
+
+export const buildProxyUrl = (proxy: Proxy): string => {
+	const { protocol, host, port, username, password } = proxy;
+	let credentials = "";
+	if (username) {
+		credentials = password ? `${encodeURIComponent(username)}:${encodeURIComponent(password)}@` : `${encodeURIComponent(username)}@`;
+	}
+	return `${protocol}://${credentials}${host}:${port}`;
+};
+
+export class ProxyResolver implements IProxyResolver {
+	static SERVICE_NAME = SERVICE_NAME;
+	constructor(
+		private proxiesRepository: IProxiesRepository,
+		private settingsService: ISettingsService,
+		private logger: ILogger,
+		private ttlMs = 60_000
+	) {}
+
+	private cache = new Map<string, { value: Promise<unknown>; expiresAt: number }>();
+
+	private getCached<T>(key: string, fetch: () => Promise<T>): Promise<T> {
+		const hit = this.cache.get(key);
+		if (hit && hit.expiresAt > Date.now()) {
+			return hit.value as Promise<T>;
+		}
+		// Cache the in flight promise so concurrent misses share one fetch
+		const value = fetch();
+		this.cache.set(key, { value, expiresAt: Date.now() + this.ttlMs });
+		// Don't negative cache rejections, evict so the next resolve retries
+		value.catch(() => this.cache.delete(key));
+		return value;
+	}
+
+	private warn(message: string, monitor: Monitor, error?: unknown) {
+		this.logger.warn({
+			message,
+			service: SERVICE_NAME,
+			method: "resolve",
+			details: {
+				monitorId: monitor.id,
+				proxyMode: monitor.proxyMode,
+				proxyId: monitor.proxyId,
+				...(error instanceof Error ? { error: error.message } : {}),
+			},
+		});
+	}
+
+	private resolveCustom = async (monitor: Monitor): Promise<string | undefined> => {
+		const { proxyId, teamId } = monitor;
+		if (!proxyId) {
+			this.warn("Proxy mode is custom, but proxyId is missing, connecting direct", monitor);
+			return undefined;
+		}
+
+		const proxy = await this.getCached(`proxy:${proxyId}:${teamId}`, () => this.proxiesRepository.findByIdOrNull(proxyId, teamId));
+		if (!proxy) {
+			this.warn("Proxy not found, connecting direct", monitor);
+			return undefined;
+		}
+		return buildProxyUrl(proxy);
+	};
+
+	private resolveInherit = async (monitor: Monitor): Promise<string | undefined> => {
+		const settings = await this.getCached("settings", () => this.settingsService.getDBSettings());
+		if (!settings.globalProxyEnabled) {
+			return undefined;
+		}
+		const globalProxyId = settings.globalProxyId;
+		if (!globalProxyId) {
+			return undefined;
+		}
+		const proxy = await this.getCached(`proxy:${globalProxyId}`, () => this.proxiesRepository.findByIdOrNull(globalProxyId));
+		if (!proxy) {
+			this.warn("Global proxy references a proxy that no longer exists, connecting direct", monitor);
+			return undefined;
+		}
+		return buildProxyUrl(proxy);
+	};
+
+	async resolve(monitor: Monitor): Promise<string | undefined> {
+		if (monitor.type !== "http") {
+			return undefined;
+		}
+		try {
+			switch (monitor.proxyMode) {
+				case "none":
+					return undefined;
+				case "custom":
+					return await this.resolveCustom(monitor);
+				default:
+					// "inherit" is the default mode
+					return await this.resolveInherit(monitor);
+			}
+		} catch (error: unknown) {
+			this.warn("Proxy resolution failed, connecting direct", monitor, error);
+			return undefined;
+		}
+	}
+}
diff --git a/server/src/service/networkService.ts b/server/src/service/networkService.ts
index 75ff66bda..69e97b092 100644
--- a/server/src/service/networkService.ts
+++ b/server/src/service/networkService.ts
@@ -1,5 +1,5 @@
 import type { Monitor, MonitorType } from "@/domain/monitors/monitor.type.js";
-import type { MonitorPayloadMap, MonitorStatusResponse } from "@/types/network.js";
+import type { CheckContext, MonitorPayloadMap, MonitorStatusResponse } from "@/types/network.js";
 import type { AxiosStatic } from "axios";
 import { AppError } from "@/utils/AppError.js";
 import { NETWORK_ERROR } from "@/types/network.js";
@@ -8,7 +8,7 @@ import { IStatusProvider } from "./network/IStatusProvider.js";
 const SERVICE_NAME = "NetworkService";
 
 export interface INetworkService {
-	requestStatus<T extends MonitorType>(monitor: Monitor & { type: T }): Promise<MonitorStatusResponse<MonitorPayloadMap[T]>>;
+	requestStatus<T extends MonitorType>(monitor: Monitor & { type: T }, ctx?: CheckContext): Promise<MonitorStatusResponse<MonitorPayloadMap[T]>>;
 	requestWebhook(
 		type: string,
 		url: string,
@@ -39,12 +39,15 @@ export class NetworkService implements INetworkService {
 	}
 
 	// Main entry point
-	async requestStatus<T extends MonitorType>(monitor: Monitor & { type: T }): Promise<MonitorStatusResponse<MonitorPayloadMap[T]>> {
+	async requestStatus<T extends MonitorType>(
+		monitor: Monitor & { type: T },
+		ctx?: CheckContext
+	): Promise<MonitorStatusResponse<MonitorPayloadMap[T]>> {
 		const provider = this.providers.find((p) => p.supports(monitor.type));
 		if (!provider) {
 			return this.handleUnsupportedType(monitor.type) as Promise<MonitorStatusResponse<MonitorPayloadMap[T]>>;
 		}
-		return provider.handle(monitor) as Promise<MonitorStatusResponse<MonitorPayloadMap[T]>>;
+		return provider.handle(monitor, ctx) as Promise<MonitorStatusResponse<MonitorPayloadMap[T]>>;
 	}
 
 	private async handleUnsupportedType(type: string): Promise<MonitorStatusResponse> {
diff --git a/server/src/types/network.ts b/server/src/types/network.ts
index 2839ed95f..0c8dd7cae 100644
--- a/server/src/types/network.ts
+++ b/server/src/types/network.ts
@@ -152,3 +152,7 @@ export type StatusChangeResult = {
 };
 
 export type MonitorStatusResponseOverrides<T> = Partial<Omit<MonitorStatusResponse<T>, "monitorId" | "teamId" | "type">>;
+
+export type CheckContext = {
+	proxyUrl?: string;
+};
diff --git a/server/src/worker/worker.check-producer.ts b/server/src/worker/worker.check-producer.ts
index b73e2c6de..f297d01be 100644
--- a/server/src/worker/worker.check-producer.ts
+++ b/server/src/worker/worker.check-producer.ts
@@ -9,6 +9,7 @@ import { ICheckService } from "@/domain/checks/check.service.js";
 import { IMonitorsRepository } from "@/domain/monitors/monitor.repository.interface.js";
 import { IMaintenanceWindowsRepository } from "@/domain/maintenance-windows/maintenance-window.repository.interface.js";
 import { isWindowActive } from "@/utils/maintenanceWindow.js";
+import { IProxyResolver } from "@/service/network/ProxyResolver.js";
 
 export interface ICheckProducer {
 	produce(monitor: Monitor): Promise<{ status: MonitorStatusResponse; check: Check } | null>;
@@ -22,6 +23,7 @@ export class CheckProducer implements ICheckProducer {
 		private maintenanceWindowsRepository: IMaintenanceWindowsRepository,
 		private checkService: ICheckService,
 		private networkService: INetworkService,
+		private proxyResolver: IProxyResolver,
 		private bufferService: IBufferService,
 		private logger: ILogger
 	) {}
@@ -56,7 +58,8 @@ export class CheckProducer implements ICheckProducer {
 		}
 
 		// Step 1b: Acquire status
-		const status = await this.networkService.requestStatus(monitor);
+		const proxyUrl = await this.proxyResolver.resolve(monitor);
+		const status = await this.networkService.requestStatus(monitor, { proxyUrl });
 		if (!status) {
 			throw new Error("No network response");
 		}
diff --git a/server/test/helpers/heartbeatTestHarness.ts b/server/test/helpers/heartbeatTestHarness.ts
index 898c3c91e..9c2161790 100644
--- a/server/test/helpers/heartbeatTestHarness.ts
+++ b/server/test/helpers/heartbeatTestHarness.ts
@@ -127,12 +127,14 @@ export function createHeartbeatTestHarness(): HeartbeatTestHarness {
 	};
 
 	const maintenanceWindowsRepo = { findByMonitorId: jest.fn().mockResolvedValue([]) };
+	const proxyResolver = { resolve: jest.fn().mockResolvedValue(undefined) };
 
 	const checkProducer = new CheckProducer(
 		monitorsRepo as any,
 		maintenanceWindowsRepo as any,
 		checkService as any,
 		networkService as any,
+		proxyResolver as any,
 		bufferStub as any,
 		logger
 	);
diff --git a/server/test/unit/providers/network/httpProvider.test.ts b/server/test/unit/providers/network/httpProvider.test.ts
index 9ab69f25d..4e559ab06 100644
--- a/server/test/unit/providers/network/httpProvider.test.ts
+++ b/server/test/unit/providers/network/httpProvider.test.ts
@@ -1,4 +1,5 @@
 import { describe, expect, it, jest } from "@jest/globals";
+import { HttpProxyAgent, HttpsProxyAgent } from "hpagent";
 import { testStatusProviderContract } from "../../../helpers/statusProviderContract.ts";
 import { NETWORK_ERROR } from "../../../../src/types/network.ts";
 import type { Monitor } from "../../../../src/domain/monitors/monitor.type.ts";
@@ -494,4 +495,152 @@ describe("HttpProvider", () => {
 			expect(advancedMatcher.validate).not.toHaveBeenCalled();
 		});
 	});
+
+	// ── Proxy support ────────────────────────────────────────────────────
+
+	describe("proxy support", () => {
+		const PROXY_URL = "http://proxy.example.com:8080";
+
+		const gotOptions = (callIndex = 0) => mockGot.mock.calls[callIndex]?.[1] as any;
+
+		const makeConnectionError = (code: string, message = `connect ${code} 10.0.0.1:8080`) => {
+			const err = new RequestError(message);
+			(err as any).code = code;
+			return err;
+		};
+
+		it("uses hpagent proxy agents when ctx.proxyUrl is set", async () => {
+			mockGot.mockResolvedValue(makeGotResponse());
+			const { provider } = createProvider();
+
+			await provider.handle(makeMonitor(), { proxyUrl: PROXY_URL });
+
+			expect(gotOptions().agent.http).toBeInstanceOf(HttpProxyAgent);
+			expect(gotOptions().agent.https).toBeInstanceOf(HttpsProxyAgent);
+		});
+
+		it("uses the shared agents when ctx has no proxyUrl", async () => {
+			mockGot.mockResolvedValue(makeGotResponse());
+			const { provider } = createProvider();
+
+			await provider.handle(makeMonitor());
+			await provider.handle(makeMonitor(), {});
+
+			expect(gotOptions(0).agent.http).not.toBeInstanceOf(HttpProxyAgent);
+			expect(gotOptions(1).agent.http).toBe(gotOptions(0).agent.http);
+			expect(gotOptions(1).agent.https).toBe(gotOptions(0).agent.https);
+		});
+
+		it("reuses the cached agent pair across checks with the same proxyUrl", async () => {
+			mockGot.mockResolvedValue(makeGotResponse());
+			const { provider } = createProvider();
+
+			await provider.handle(makeMonitor(), { proxyUrl: PROXY_URL });
+			await provider.handle(makeMonitor(), { proxyUrl: PROXY_URL });
+
+			expect(gotOptions(1).agent.http).toBe(gotOptions(0).agent.http);
+			expect(gotOptions(1).agent.https).toBe(gotOptions(0).agent.https);
+		});
+
+		it("builds distinct agent pairs for distinct proxyUrls", async () => {
+			mockGot.mockResolvedValue(makeGotResponse());
+			const { provider } = createProvider();
+
+			await provider.handle(makeMonitor(), { proxyUrl: PROXY_URL });
+			await provider.handle(makeMonitor(), { proxyUrl: "http://other.example.com:3128" });
+
+			expect(gotOptions(1).agent.http).not.toBe(gotOptions(0).agent.http);
+		});
+
+		it("builds distinct pairs per ignoreTlsErrors and sets rejectUnauthorized accordingly", async () => {
+			mockGot.mockResolvedValue(makeGotResponse());
+			const { provider } = createProvider();
+
+			await provider.handle(makeMonitor({ ignoreTlsErrors: false }), { proxyUrl: PROXY_URL });
+			await provider.handle(makeMonitor({ ignoreTlsErrors: true }), { proxyUrl: PROXY_URL });
+
+			expect(gotOptions(1).agent.https).not.toBe(gotOptions(0).agent.https);
+			expect(gotOptions(0).agent.https.options.rejectUnauthorized).toBe(true);
+			expect(gotOptions(1).agent.https.options.rejectUnauthorized).toBe(false);
+		});
+
+		it("evicts and destroys the least-recently-used pair past the cache cap", async () => {
+			mockGot.mockResolvedValue(makeGotResponse());
+			const { provider } = createProvider();
+
+			await provider.handle(makeMonitor(), { proxyUrl: "http://proxy0.example.com:8080" });
+			const first = gotOptions(0).agent;
+			const httpDestroy = jest.spyOn(first.http, "destroy");
+			const httpsDestroy = jest.spyOn(first.https, "destroy");
+
+			for (let i = 1; i <= 49; i++) {
+				await provider.handle(makeMonitor(), { proxyUrl: `http://proxy${i}.example.com:8080` });
+			}
+			expect(httpDestroy).not.toHaveBeenCalled();
+
+			await provider.handle(makeMonitor(), { proxyUrl: "http://proxy50.example.com:8080" });
+
+			expect(httpDestroy).toHaveBeenCalled();
+			expect(httpsDestroy).toHaveBeenCalled();
+			// The evicted pair is gone — the same proxyUrl now gets a fresh pair
+			await provider.handle(makeMonitor(), { proxyUrl: "http://proxy0.example.com:8080" });
+			expect(gotOptions(51).agent.http).not.toBe(first.http);
+		});
+
+		it("names the proxy in the message when the proxy connection fails", async () => {
+			mockGot.mockRejectedValue(makeConnectionError("ECONNREFUSED"));
+			const { provider } = createProvider();
+
+			const result = await provider.handle(makeMonitor(), { proxyUrl: PROXY_URL });
+
+			expect(result.status).toBe(false);
+			expect(result.code).toBe(NETWORK_ERROR);
+			expect(result.message).toBe("Proxy connection failed (proxy.example.com:8080): connect ECONNREFUSED 10.0.0.1:8080");
+		});
+
+		it("does not attribute timeouts to the proxy", async () => {
+			mockGot.mockRejectedValue(makeConnectionError("ETIMEDOUT", "Timeout awaiting 'request' for 30000ms"));
+			const { provider } = createProvider();
+
+			const result = await provider.handle(makeMonitor(), { proxyUrl: PROXY_URL });
+
+			expect(result.status).toBe(false);
+			expect(result.message).toBe("Timeout awaiting 'request' for 30000ms");
+		});
+
+		it("leaves connection-error messages unprefixed for direct checks", async () => {
+			mockGot.mockRejectedValue(makeConnectionError("ECONNREFUSED"));
+			const { provider } = createProvider();
+
+			const result = await provider.handle(makeMonitor());
+
+			expect(result.message).toBe("connect ECONNREFUSED 10.0.0.1:8080");
+		});
+
+		it("never leaks proxy credentials into the message", async () => {
+			mockGot.mockRejectedValue(makeConnectionError("ECONNREFUSED"));
+			const { provider } = createProvider();
+
+			const result = await provider.handle(makeMonitor(), { proxyUrl: "http://bob:sekret@proxy.example.com:8080" });
+
+			expect(result.message).toContain("proxy.example.com:8080");
+			expect(result.message).not.toContain("bob");
+			expect(result.message).not.toContain("sekret");
+		});
+
+		it("does not prefix errors that carry a response (target failure through a healthy proxy)", async () => {
+			const err = new RequestError("Response code 500 (Internal Server Error)");
+			(err as any).code = "ECONNRESET";
+			(err as any).response = { statusCode: 500, body: "", headers: {} };
+			(err as any).timings = { phases: { total: 25 } };
+			mockGot.mockRejectedValue(err);
+			const { provider } = createProvider();
+
+			const result = await provider.handle(makeMonitor(), { proxyUrl: PROXY_URL });
+
+			expect(result.status).toBe(false);
+			expect(result.code).toBe(500);
+			expect(result.message).toBe("Response code 500 (Internal Server Error)");
+		});
+	});
 });
diff --git a/server/test/unit/services/checkProducer.test.ts b/server/test/unit/services/checkProducer.test.ts
index dacff3d9b..2a1aa29f1 100644
--- a/server/test/unit/services/checkProducer.test.ts
+++ b/server/test/unit/services/checkProducer.test.ts
@@ -26,6 +26,7 @@ const createProducer = (overrides?: Record<string, any>) => {
 		maintenanceWindowsRepository: { findByMonitorId: jest.fn().mockResolvedValue([]) },
 		checkService: { toCheck: jest.fn().mockReturnValue({ id: "check-1" }) },
 		networkService: { requestStatus: jest.fn().mockResolvedValue({ monitorId: "m1", status: true, code: 200, message: "OK" }) },
+		proxyResolver: { resolve: jest.fn().mockResolvedValue(undefined) },
 		buffer: { addToBuffer: jest.fn() },
 		...overrides,
 	};
@@ -34,6 +35,7 @@ const createProducer = (overrides?: Record<string, any>) => {
 		defaults.maintenanceWindowsRepository as any,
 		defaults.checkService as any,
 		defaults.networkService as any,
+		defaults.proxyResolver as any,
 		defaults.buffer as any,
 		defaults.logger as any
 	);
@@ -82,6 +84,29 @@ describe("CheckProducer", () => {
 		expect(defaults.networkService.requestStatus).toHaveBeenCalled();
 	});
 
+	// ── proxy resolution ──────────────────────────────────────────────────────
+
+	it("passes the resolved proxy url into requestStatus", async () => {
+		const { producer, defaults } = createProducer({
+			proxyResolver: { resolve: jest.fn().mockResolvedValue("http://proxy.example.com:8080") },
+		});
+		const monitor = makeMonitor();
+
+		await producer.produce(monitor);
+
+		expect(defaults.networkService.requestStatus).toHaveBeenCalledWith(monitor, { proxyUrl: "http://proxy.example.com:8080" });
+	});
+
+	it("still produces a check when the resolver returns undefined", async () => {
+		const { producer, defaults } = createProducer();
+		const monitor = makeMonitor();
+
+		const result = await producer.produce(monitor);
+
+		expect(defaults.networkService.requestStatus).toHaveBeenCalledWith(monitor, { proxyUrl: undefined });
+		expect(result).toEqual({ status: expect.objectContaining({ monitorId: "m1" }), check: { id: "check-1" } });
+	});
+
 	// ── acquire / record ──────────────────────────────────────────────────────
 
 	it("throws when the network response is null", async () => {
diff --git a/server/test/unit/services/networkService.test.ts b/server/test/unit/services/networkService.test.ts
index 2e6627452..b33983bf9 100644
--- a/server/test/unit/services/networkService.test.ts
+++ b/server/test/unit/services/networkService.test.ts
@@ -54,7 +54,7 @@ describe("NetworkService", () => {
 			const result = await service.requestStatus(monitor);
 
 			expect(provider.supports).toHaveBeenCalledWith("http");
-			expect(provider.handle).toHaveBeenCalledWith(monitor);
+			expect(provider.handle).toHaveBeenCalledWith(monitor, undefined);
 			expect(result).toEqual(
 				expect.objectContaining({
 					monitorId: "mon-1",
@@ -73,7 +73,18 @@ describe("NetworkService", () => {
 			await service.requestStatus(monitor);
 
 			expect(httpProvider.handle).not.toHaveBeenCalled();
-			expect(pingProvider.handle).toHaveBeenCalledWith(monitor);
+			expect(pingProvider.handle).toHaveBeenCalledWith(monitor, undefined);
+		});
+
+		it("forwards the check context to the provider", async () => {
+			const provider = createMockProvider("http");
+			const { service } = createService([provider]);
+			const monitor = { type: "http", _id: "mon-1" } as unknown as Monitor & { type: "http" };
+			const ctx = { proxyUrl: "http://proxy.example.com:8080" };
+
+			await service.requestStatus(monitor, ctx);
+
+			expect(provider.handle).toHaveBeenCalledWith(monitor, ctx);
 		});
 
 		it("returns unsupported-type response when no provider matches", async () => {
diff --git a/server/test/unit/services/proxyResolver.test.ts b/server/test/unit/services/proxyResolver.test.ts
new file mode 100644
index 000000000..d2c5eefa2
--- /dev/null
+++ b/server/test/unit/services/proxyResolver.test.ts
@@ -0,0 +1,267 @@
+import { describe, expect, it, jest } from "@jest/globals";
+import { ProxyResolver, buildProxyUrl } from "../../../src/service/network/ProxyResolver.ts";
+import type { Monitor } from "../../../src/domain/monitors/monitor.type.ts";
+import type { Proxy } from "../../../src/domain/proxies/proxy.type.ts";
+import { createMockLogger } from "../../helpers/createMockLogger.ts";
+
+const makeMonitor = (overrides?: Partial<Monitor>): Monitor =>
+	({
+		id: "m1",
+		teamId: "team",
+		type: "http",
+		proxyMode: "inherit",
+		...overrides,
+	}) as Monitor;
+
+const makeProxy = (overrides?: Partial<Proxy>): Proxy =>
+	({
+		id: "p1",
+		teamId: "team",
+		name: "corp",
+		protocol: "http",
+		host: "proxy.example.com",
+		port: 8080,
+		...overrides,
+	}) as Proxy;
+
+const createResolver = (overrides?: Record<string, any>) => {
+	const defaults = {
+		proxiesRepository: { findByIdOrNull: jest.fn<() => Promise<Proxy | null>>().mockResolvedValue(makeProxy()) },
+		settingsService: { getDBSettings: jest.fn<() => Promise<any>>().mockResolvedValue({ globalProxyEnabled: true, globalProxyId: "p1" }) },
+		logger: createMockLogger(),
+		ttlMs: 60_000,
+		...overrides,
+	};
+	const resolver = new ProxyResolver(defaults.proxiesRepository as any, defaults.settingsService as any, defaults.logger as any, defaults.ttlMs);
+	return { resolver, defaults };
+};
+
+describe("ProxyResolver", () => {
+	// ── gates ─────────────────────────────────────────────────────────────────
+
+	it("returns undefined for non-http monitors without touching repo or settings", async () => {
+		const { resolver, defaults } = createResolver();
+
+		const result = await resolver.resolve(makeMonitor({ type: "port", proxyMode: "custom", proxyId: "p1" } as Partial<Monitor>));
+
+		expect(result).toBeUndefined();
+		expect(defaults.proxiesRepository.findByIdOrNull).not.toHaveBeenCalled();
+		expect(defaults.settingsService.getDBSettings).not.toHaveBeenCalled();
+	});
+
+	it("returns undefined for proxyMode 'none' without calling settings", async () => {
+		const { resolver, defaults } = createResolver();
+
+		const result = await resolver.resolve(makeMonitor({ proxyMode: "none" }));
+
+		expect(result).toBeUndefined();
+		expect(defaults.settingsService.getDBSettings).not.toHaveBeenCalled();
+	});
+
+	// ── custom mode ───────────────────────────────────────────────────────────
+
+	it("resolves a custom proxy with a team-scoped lookup", async () => {
+		const { resolver, defaults } = createResolver();
+
+		const result = await resolver.resolve(makeMonitor({ proxyMode: "custom", proxyId: "p1" }));
+
+		expect(result).toBe("http://proxy.example.com:8080");
+		expect(defaults.proxiesRepository.findByIdOrNull).toHaveBeenCalledWith("p1", "team");
+	});
+
+	it("returns undefined and warns when the custom proxy no longer exists", async () => {
+		const { resolver, defaults } = createResolver({
+			proxiesRepository: { findByIdOrNull: jest.fn<() => Promise<Proxy | null>>().mockResolvedValue(null) },
+		});
+
+		const result = await resolver.resolve(makeMonitor({ proxyMode: "custom", proxyId: "gone" }));
+
+		expect(result).toBeUndefined();
+		expect(defaults.logger.warn).toHaveBeenCalled();
+	});
+
+	it("returns undefined and warns when proxyMode is custom but proxyId is missing, without a repo call", async () => {
+		const { resolver, defaults } = createResolver();
+
+		const result = await resolver.resolve(makeMonitor({ proxyMode: "custom", proxyId: undefined }));
+
+		expect(result).toBeUndefined();
+		expect(defaults.logger.warn).toHaveBeenCalled();
+		expect(defaults.proxiesRepository.findByIdOrNull).not.toHaveBeenCalled();
+	});
+
+	// ── inherit mode ──────────────────────────────────────────────────────────
+
+	it("returns undefined when the global proxy is disabled, without a repo call", async () => {
+		const { resolver, defaults } = createResolver({
+			settingsService: { getDBSettings: jest.fn<() => Promise<any>>().mockResolvedValue({ globalProxyEnabled: false, globalProxyId: "p1" }) },
+		});
+
+		const result = await resolver.resolve(makeMonitor({ proxyMode: "inherit" }));
+
+		expect(result).toBeUndefined();
+		expect(defaults.proxiesRepository.findByIdOrNull).not.toHaveBeenCalled();
+	});
+
+	it("resolves the global proxy with an unscoped lookup when enabled", async () => {
+		const { resolver, defaults } = createResolver();
+
+		const result = await resolver.resolve(makeMonitor({ proxyMode: "inherit" }));
+
+		expect(result).toBe("http://proxy.example.com:8080");
+		expect(defaults.proxiesRepository.findByIdOrNull).toHaveBeenCalledWith("p1");
+	});
+
+	it("returns undefined when the global proxy is enabled but globalProxyId is null, without a repo call", async () => {
+		const { resolver, defaults } = createResolver({
+			settingsService: { getDBSettings: jest.fn<() => Promise<any>>().mockResolvedValue({ globalProxyEnabled: true, globalProxyId: null }) },
+		});
+
+		const result = await resolver.resolve(makeMonitor({ proxyMode: "inherit" }));
+
+		expect(result).toBeUndefined();
+		expect(defaults.proxiesRepository.findByIdOrNull).not.toHaveBeenCalled();
+	});
+
+	it("returns undefined and warns when the global proxy references a proxy that no longer exists", async () => {
+		const { resolver, defaults } = createResolver({
+			proxiesRepository: { findByIdOrNull: jest.fn<() => Promise<Proxy | null>>().mockResolvedValue(null) },
+		});
+
+		const result = await resolver.resolve(makeMonitor({ proxyMode: "inherit" }));
+
+		expect(result).toBeUndefined();
+		expect(defaults.logger.warn).toHaveBeenCalled();
+	});
+
+	it("treats an unknown proxyMode as inherit", async () => {
+		const { resolver, defaults } = createResolver();
+
+		const result = await resolver.resolve(makeMonitor({ proxyMode: "garbage" as Monitor["proxyMode"] }));
+
+		expect(result).toBe("http://proxy.example.com:8080");
+		expect(defaults.settingsService.getDBSettings).toHaveBeenCalled();
+	});
+
+	// ── never throws ──────────────────────────────────────────────────────────
+
+	it("returns undefined and warns when the repository throws", async () => {
+		const { resolver, defaults } = createResolver({
+			proxiesRepository: { findByIdOrNull: jest.fn<() => Promise<Proxy | null>>().mockRejectedValue(new Error("db down")) },
+		});
+
+		const result = await resolver.resolve(makeMonitor({ proxyMode: "custom", proxyId: "p1" }));
+
+		expect(result).toBeUndefined();
+		expect(defaults.logger.warn).toHaveBeenCalled();
+	});
+
+	it("returns undefined and warns when the settings service throws", async () => {
+		const { resolver, defaults } = createResolver({
+			settingsService: { getDBSettings: jest.fn<() => Promise<any>>().mockRejectedValue(new Error("db down")) },
+		});
+
+		const result = await resolver.resolve(makeMonitor({ proxyMode: "inherit" }));
+
+		expect(result).toBeUndefined();
+		expect(defaults.logger.warn).toHaveBeenCalled();
+	});
+
+	// ── caching ───────────────────────────────────────────────────────────────
+
+	it("serves a second resolve within the TTL from cache", async () => {
+		const { resolver, defaults } = createResolver();
+
+		await resolver.resolve(makeMonitor({ proxyMode: "inherit" }));
+		await resolver.resolve(makeMonitor({ proxyMode: "inherit" }));
+
+		expect(defaults.settingsService.getDBSettings).toHaveBeenCalledTimes(1);
+		expect(defaults.proxiesRepository.findByIdOrNull).toHaveBeenCalledTimes(1);
+	});
+
+	it("refetches after the TTL expires", async () => {
+		const { resolver, defaults } = createResolver({ ttlMs: 0 });
+
+		await resolver.resolve(makeMonitor({ proxyMode: "inherit" }));
+		await resolver.resolve(makeMonitor({ proxyMode: "inherit" }));
+
+		expect(defaults.settingsService.getDBSettings).toHaveBeenCalledTimes(2);
+		expect(defaults.proxiesRepository.findByIdOrNull).toHaveBeenCalledTimes(2);
+	});
+
+	it("negative-caches a dangling ref, costing one repo call per TTL window", async () => {
+		const { resolver, defaults } = createResolver({
+			proxiesRepository: { findByIdOrNull: jest.fn<() => Promise<Proxy | null>>().mockResolvedValue(null) },
+		});
+
+		await resolver.resolve(makeMonitor({ proxyMode: "custom", proxyId: "gone" }));
+		await resolver.resolve(makeMonitor({ proxyMode: "custom", proxyId: "gone" }));
+
+		expect(defaults.proxiesRepository.findByIdOrNull).toHaveBeenCalledTimes(1);
+	});
+
+	it("shares one in-flight fetch between concurrent resolves", async () => {
+		const { resolver, defaults } = createResolver();
+
+		await Promise.all([
+			resolver.resolve(makeMonitor({ proxyMode: "inherit" })),
+			resolver.resolve(makeMonitor({ proxyMode: "inherit" })),
+			resolver.resolve(makeMonitor({ proxyMode: "inherit" })),
+		]);
+
+		expect(defaults.settingsService.getDBSettings).toHaveBeenCalledTimes(1);
+		expect(defaults.proxiesRepository.findByIdOrNull).toHaveBeenCalledTimes(1);
+	});
+
+	it("does not cache a rejected fetch — the next resolve retries", async () => {
+		const findByIdOrNull = jest.fn<() => Promise<Proxy | null>>().mockRejectedValueOnce(new Error("db down")).mockResolvedValueOnce(makeProxy());
+		const { resolver } = createResolver({ proxiesRepository: { findByIdOrNull } });
+
+		const first = await resolver.resolve(makeMonitor({ proxyMode: "custom", proxyId: "p1" }));
+		const second = await resolver.resolve(makeMonitor({ proxyMode: "custom", proxyId: "p1" }));
+
+		expect(first).toBeUndefined();
+		expect(second).toBe("http://proxy.example.com:8080");
+		expect(findByIdOrNull).toHaveBeenCalledTimes(2);
+	});
+
+	it("does not let a scoped miss poison the unscoped global lookup for the same proxy id", async () => {
+		const findByIdOrNull = jest.fn<(proxyId: string, teamId?: string) => Promise<Proxy | null>>(async (_proxyId, teamId) =>
+			teamId ? null : makeProxy()
+		);
+		const { resolver } = createResolver({ proxiesRepository: { findByIdOrNull } });
+
+		const customResult = await resolver.resolve(makeMonitor({ proxyMode: "custom", proxyId: "p1" }));
+		const inheritResult = await resolver.resolve(makeMonitor({ proxyMode: "inherit" }));
+
+		expect(customResult).toBeUndefined();
+		expect(inheritResult).toBe("http://proxy.example.com:8080");
+		expect(findByIdOrNull).toHaveBeenCalledTimes(2);
+	});
+});
+
+describe("buildProxyUrl", () => {
+	it("builds a URL without credentials when there is no username", () => {
+		expect(buildProxyUrl(makeProxy())).toBe("http://proxy.example.com:8080");
+	});
+
+	it("builds a URL with username and password", () => {
+		expect(buildProxyUrl(makeProxy({ username: "user", password: "pass" }))).toBe("http://user:pass@proxy.example.com:8080");
+	});
+
+	it("percent-encodes credentials", () => {
+		expect(buildProxyUrl(makeProxy({ username: "user@x", password: "p@ss" }))).toBe("http://user%40x:p%40ss@proxy.example.com:8080");
+	});
+
+	it("builds a URL with a username only, without a colon", () => {
+		expect(buildProxyUrl(makeProxy({ username: "user" }))).toBe("http://user@proxy.example.com:8080");
+	});
+
+	it("emits no credentials for a password without a username", () => {
+		expect(buildProxyUrl(makeProxy({ password: "pass" }))).toBe("http://proxy.example.com:8080");
+	});
+
+	it("uses the https scheme without a trailing slash", () => {
+		expect(buildProxyUrl(makeProxy({ protocol: "https" }))).toBe("https://proxy.example.com:8080");
+	});
+});