diff --git a/src/main/__test__/context-handler.test.ts b/src/main/__test__/context-handler.test.ts
index 5d11dbdf70..504e352ea6 100644
--- a/src/main/__test__/context-handler.test.ts
+++ b/src/main/__test__/context-handler.test.ts
@@ -3,7 +3,7 @@
  * Licensed under MIT License. See LICENSE in root directory for more information.
  */
 
-import type { ClusterContextHandler } from "../context-handler/context-handler";
+import type { ClusterContextHandler, PrometheusDetails } from "../context-handler/context-handler";
 import { getDiForUnitTesting } from "../getDiForUnitTesting";
 import createContextHandlerInjectable from "../context-handler/create-context-handler.injectable";
 import type { Cluster } from "../../common/cluster/cluster";
@@ -13,15 +13,28 @@ import { getInjectable } from "@ogre-tools/injectable";
 import type { PrometheusProvider } from "../prometheus/provider";
 import { prometheusProviderInjectionToken } from "../prometheus/provider";
 import { runInAction } from "mobx";
+import createClusterInjectable from "../create-cluster/create-cluster.injectable";
+import directoryForUserDataInjectable from "../../common/app-paths/directory-for-user-data/directory-for-user-data.injectable";
+import directoryForTempInjectable from "../../common/app-paths/directory-for-temp/directory-for-temp.injectable";
+import type { KubeAuthProxy } from "../kube-auth-proxy/kube-auth-proxy";
+import createKubeconfigManagerInjectable from "../kubeconfig-manager/create-kubeconfig-manager.injectable";
+import type { KubeconfigManager } from "../kubeconfig-manager/kubeconfig-manager";
+import type { AsyncFnMock } from "@async-fn/jest";
+import type { ReadFile } from "../../common/fs/read-file.injectable";
+import asyncFn from "@async-fn/jest";
+import readFileInjectable from "../../common/fs/read-file.injectable";
+import jsyaml from "js-yaml";
+import type { AsyncResult } from "../../common/utils/async-result";
+import assert from "assert";
 
 enum ServiceResult {
   Success,
   Failure,
 }
 
-const createTestPrometheusProvider = (kind: string, alwaysFail: ServiceResult): PrometheusProvider => ({
+const createTestPrometheusProvider = (kind: string, name: string, alwaysFail: ServiceResult): PrometheusProvider => ({
   kind,
-  name: "TestProvider1",
+  name,
   isConfigurable: false,
   getQuery: () => {
     throw new Error("getQuery is not implemented.");
@@ -41,151 +54,232 @@ const createTestPrometheusProvider = (kind: string, alwaysFail: ServiceResult):
   },
 });
 
-const clusterStub = {
-  getProxyKubeconfig: () => ({
-    makeApiClient: (): void => undefined,
-  }),
-  apiUrl: "http://localhost:81",
-} as unknown as Cluster;
+const proxyConfigValue = jsyaml.dump({
+  apiVersion: "v1",
+  clusters: [{
+    cluster: {
+      server: "https://127.0.0.1:55009",
+    },
+    name: "some-cluster-name",
+  }],
+  users: [{
+    name: "some-user-name",
+    user: {
+      "client-certificate": "/some/path/to/client-cert",
+      "client-key": "/some/path/to/client-key",
+    },
+  }],
+  contexts: [{
+    name: "some-proxy-context",
+    context: {
+      user: "some-user-name",
+      cluster: "some-cluster-name",
+    },
+  }],
+  "current-context": "some-proxy-context",
+});
 
 describe("ContextHandler", () => {
   let createContextHandler: (cluster: Cluster) => ClusterContextHandler;
   let di: DiContainer;
+  let cluster: Cluster;
+  let readFileMock: AsyncFnMock<ReadFile>;
 
   beforeEach(() => {
     di = getDiForUnitTesting({ doGeneralOverrides: true });
-    di.override(createKubeAuthProxyInjectable, () => ({} as any));
+    di.override(createKubeAuthProxyInjectable, () => () => ({
+      run: async () => {},
+    } as Partial<KubeAuthProxy> as KubeAuthProxy));
+    di.override(createKubeconfigManagerInjectable, () => () => ({
+      getPath: async () => "/some/proxy-kubeconfig",
+    } as Partial<KubeconfigManager> as KubeconfigManager));
+    di.override(directoryForUserDataInjectable, () => "/some-directory-for-user-data");
+    di.override(directoryForTempInjectable, () => "/some-directory-for-temp-data");
+
+    readFileMock = asyncFn();
+    di.override(readFileInjectable, () => readFileMock);
 
     createContextHandler = di.inject(createContextHandlerInjectable);
+
+    const createCluster = di.inject(createClusterInjectable);
+
+    cluster = createCluster({
+      contextName: "some-context-name",
+      id: "some-cluster-id",
+      kubeConfigPath: "/some/path/to/kubeconfig",
+    }, {
+      clusterServerUrl: "http://localhost:81",
+    });
   });
 
   describe("getPrometheusService", () => {
-    it.each([
-      [0],
-      [1],
-      [2],
-      [3],
-    ])("should throw after %d failure(s)", async (failures) => {
-      runInAction(() => {
-        for (let i = 0; i < failures; i += 1) {
-          di.register(getInjectable({
-            id: `test-prometheus-provider-failure-${i}`,
-            injectionToken: prometheusProviderInjectionToken,
-            instantiate: () => createTestPrometheusProvider(`id_failure_${i}`, ServiceResult.Failure),
-          }));
-        }
+    for (let failures = 0; failures < 4; failures += 1) {
+      describe(`with ${failures} providers that throw`, () => {
+        beforeEach(() => {
+          runInAction(() => {
+            for (let i = 0; i < failures; i += 1) {
+              di.register(getInjectable({
+                id: `test-prometheus-provider-failure-${i}`,
+                injectionToken: prometheusProviderInjectionToken,
+                instantiate: () => createTestPrometheusProvider(`id_failure_${i}`, `TestService-${i}`, ServiceResult.Failure),
+              }));
+            }
+          });
+        });
+
+        describe("when getting prometheus details", () => {
+          let details: Promise<AsyncResult<PrometheusDetails, Error>>;
+
+          beforeEach(() => {
+            details = createContextHandler(cluster).getPrometheusDetails();
+          });
+
+          it("should read the proxy config file", () => {
+            expect(readFileMock).toBeCalledWith("/some/proxy-kubeconfig");
+          });
+
+          describe("when reading the proxy config file resolves", () => {
+            beforeEach(async () => {
+              await readFileMock.resolveSpecific(
+                ["/some/proxy-kubeconfig"],
+                proxyConfigValue,
+              );
+            });
+
+            it("should resolve with a failed call", async () => {
+              await expect(details).resolves.toMatchObject({ callWasSuccessful: false });
+            });
+          });
+        });
       });
+    }
 
-      expect(() => createContextHandler(clusterStub).getPrometheusDetails()).rejects.toThrowError();
-    });
+    for (let successes = 1; successes < 3; successes += 1) {
+      for (let failures = 0; failures < 4; failures += 1) {
+        describe(`with ${successes} successful providers followed by ${failures} erroring providers`, () => {
+          beforeEach(() => {
+            runInAction(() => {
+              for (let i = 0; i < failures; i += 1) {
+                di.register(getInjectable({
+                  id: `test-prometheus-provider-failure-${i}`,
+                  injectionToken: prometheusProviderInjectionToken,
+                  instantiate: () => createTestPrometheusProvider(`id_failure_${i}`, `TestService-${i}`, ServiceResult.Failure),
+                }));
+              }
 
-    it.each([
-      [1, 0],
-      [1, 1],
-      [1, 2],
-      [1, 3],
-      [2, 0],
-      [2, 1],
-      [2, 2],
-      [2, 3],
-    ])("should pick the first provider of %d success(es) after %d failure(s)", async (successes, failures) => {
-      runInAction(() => {
-        for (let i = 0; i < failures; i += 1) {
-          di.register(getInjectable({
-            id: `test-prometheus-provider-failure-${i}`,
-            injectionToken: prometheusProviderInjectionToken,
-            instantiate: () => createTestPrometheusProvider(`id_failure_${i}`, ServiceResult.Failure),
-          }));
-        }
+              for (let i = 0; i < successes; i += 1) {
+                di.register(getInjectable({
+                  id: `test-prometheus-provider-success-${i}`,
+                  injectionToken: prometheusProviderInjectionToken,
+                  instantiate: () => createTestPrometheusProvider(`id_success_${i}`, `TestService-${i+10}`, ServiceResult.Success),
+                }));
+              }
+            });
+          });
 
-        for (let i = 0; i < successes; i += 1) {
-          di.register(getInjectable({
-            id: `test-prometheus-provider-success-${i}`,
-            injectionToken: prometheusProviderInjectionToken,
-            instantiate: () => createTestPrometheusProvider(`id_success_${i}`, ServiceResult.Success),
-          }));
-        }
-      });
+          describe("when getting prometheus details", () => {
+            let details: Promise<AsyncResult<PrometheusDetails, Error>>;
 
-      const details = await createContextHandler(clusterStub).getPrometheusDetails();
+            beforeEach(() => {
+              details = createContextHandler(cluster).getPrometheusDetails();
+            });
 
-      expect(details.provider.kind === `id_failure_${failures}`);
-    });
+            it("should read the proxy config file", () => {
+              expect(readFileMock).toBeCalledWith("/some/proxy-kubeconfig");
+            });
 
-    it.each([
-      [1, 0],
-      [1, 1],
-      [1, 2],
-      [1, 3],
-      [2, 0],
-      [2, 1],
-      [2, 2],
-      [2, 3],
-    ])("should pick the first provider of %d success(es) before %d failure(s)", async (successes, failures) => {
-      runInAction(() => {
-        for (let i = 0; i < failures; i += 1) {
-          di.register(getInjectable({
-            id: `test-prometheus-provider-failure-${i}`,
-            injectionToken: prometheusProviderInjectionToken,
-            instantiate: () => createTestPrometheusProvider(`id_failure_${i}`, ServiceResult.Failure),
-          }));
-        }
+            describe("when reading the proxy config file resolves", () => {
+              beforeEach(async () => {
+                await readFileMock.resolveSpecific(
+                  ["/some/proxy-kubeconfig"],
+                  proxyConfigValue,
+                );
+              });
 
-        for (let i = 0; i < successes; i += 1) {
-          di.register(getInjectable({
-            id: `test-prometheus-provider-success-${i}`,
-            injectionToken: prometheusProviderInjectionToken,
-            instantiate: () => createTestPrometheusProvider(`id_success_${i}`, ServiceResult.Success),
-          }));
-        }
-      });
+              it("should resolve with the first success provider", async () => {
+                const result = await details;
 
-      const details = await createContextHandler(clusterStub).getPrometheusDetails();
+                assert(result.callWasSuccessful);
 
-      expect(details.provider.kind === "id_failure_0");
-    });
+                expect(result.response).toMatchObject({
+                  provider: {
+                    kind: `id_success_0`,
+                  },
+                });
+              });
+            });
+          });
+        });
+      }
+    }
 
-    it.each([
-      [1, 0],
-      [1, 1],
-      [1, 2],
-      [1, 3],
-      [2, 0],
-      [2, 1],
-      [2, 2],
-      [2, 3],
-    ])("should pick the first provider of %d success(es) between %d failure(s)", async (successes, failures) => {
-      const beforeSuccesses = Math.floor(successes / 2);
+    for (let successes = 1; successes < 3; successes += 1) {
+      for (let failures = 0; failures < 4; failures += 1) {
+        const beforeSuccesses = Math.floor(successes / 2);
 
-      runInAction(() => {
-        for (let i = 0; i < beforeSuccesses; i += 1) {
-          di.register(getInjectable({
-            id: `test-prometheus-provider-success-${i}`,
-            injectionToken: prometheusProviderInjectionToken,
-            instantiate: () => createTestPrometheusProvider(`id_success_${i}`, ServiceResult.Success),
-          }));
-        }
+        describe(`with ${successes} successful providers between by ${failures} erroring providers`, () => {
+          beforeEach(() => {
+            runInAction(() => {
+              for (let i = 0; i < beforeSuccesses; i += 1) {
+                di.register(getInjectable({
+                  id: `test-prometheus-provider-success-${i}`,
+                  injectionToken: prometheusProviderInjectionToken,
+                  instantiate: () => createTestPrometheusProvider(`id_success_${i}`, `TestService-${i}`, ServiceResult.Success),
+                }));
+              }
 
-        for (let i = 0; i < failures; i += 1) {
-          di.register(getInjectable({
-            id: `test-prometheus-provider-failure-${i}`,
-            injectionToken: prometheusProviderInjectionToken,
-            instantiate: () => createTestPrometheusProvider(`id_failure_${i}`, ServiceResult.Failure),
-          }));
-        }
+              for (let i = 0; i < failures; i += 1) {
+                di.register(getInjectable({
+                  id: `test-prometheus-provider-failure-${i}`,
+                  injectionToken: prometheusProviderInjectionToken,
+                  instantiate: () => createTestPrometheusProvider(`id_failure_${i}`, `TestService-${i+10}`, ServiceResult.Failure),
+                }));
+              }
 
-        for (let i = beforeSuccesses; i < successes; i += 1) {
-          di.register(getInjectable({
-            id: `test-prometheus-provider-success-${i}`,
-            injectionToken: prometheusProviderInjectionToken,
-            instantiate: () => createTestPrometheusProvider(`id_success_${i}`, ServiceResult.Success),
-          }));
-        }
-      });
+              for (let i = beforeSuccesses; i < successes; i += 1) {
+                di.register(getInjectable({
+                  id: `test-prometheus-provider-success-${i}`,
+                  injectionToken: prometheusProviderInjectionToken,
+                  instantiate: () => createTestPrometheusProvider(`id_success_${i}`, `TestService-${i+20}`, ServiceResult.Success),
+                }));
+              }
+            });
+          });
 
-      const details = await createContextHandler(clusterStub).getPrometheusDetails();
+          describe("when getting prometheus details", () => {
+            let details: Promise<AsyncResult<PrometheusDetails, Error>>;
 
-      expect(details.provider.kind === "id_success_0");
-    });
+            beforeEach(() => {
+              details = createContextHandler(cluster).getPrometheusDetails();
+            });
+
+            it("should read the proxy config file", () => {
+              expect(readFileMock).toBeCalledWith("/some/proxy-kubeconfig");
+            });
+
+            describe("when reading the proxy config file resolves", () => {
+              beforeEach(async () => {
+                await readFileMock.resolveSpecific(
+                  ["/some/proxy-kubeconfig"],
+                  proxyConfigValue,
+                );
+              });
+
+              it("should resolve with the first success provider", async () => {
+                const result = await details;
+
+                assert(result.callWasSuccessful);
+
+                expect(result.response).toMatchObject({
+                  provider: {
+                    kind: `id_success_0`,
+                  },
+                });
+              });
+            });
+          });
+        });
+      }
+    }
   });
 });
diff --git a/src/main/context-handler/context-handler.ts b/src/main/context-handler/context-handler.ts
index 583c18acc1..6374bef12b 100644
--- a/src/main/context-handler/context-handler.ts
+++ b/src/main/context-handler/context-handler.ts
@@ -9,6 +9,7 @@ import type { Cluster } from "../../common/cluster/cluster";
 import type httpProxy from "http-proxy";
 import type { UrlWithStringQuery } from "url";
 import url from "url";
+import type { KubeConfig } from "@kubernetes/client-node";
 import { CoreV1Api } from "@kubernetes/client-node";
 import type { KubeAuthProxy } from "../kube-auth-proxy/kube-auth-proxy";
 import type { CreateKubeAuthProxy } from "../kube-auth-proxy/create-kube-auth-proxy.injectable";
@@ -16,6 +17,7 @@ import type { GetPrometheusProviderByKind } from "../prometheus/get-by-kind.inje
 import type { IComputedValue } from "mobx";
 import type { Logger } from "../../common/logger";
 import type { MakeApiClient } from "../../common/cluster/make-api-client.injectable";
+import type { AsyncResult } from "../../common/utils/async-result";
 
 export interface PrometheusDetails {
   prometheusPath: string;
@@ -41,7 +43,7 @@ export interface ContextHandlerDependencies {
 export interface ClusterContextHandler {
   readonly clusterUrl: UrlWithStringQuery;
   setupPrometheus(preferences?: ClusterPrometheusPreferences): void;
-  getPrometheusDetails(): Promise<PrometheusDetails>;
+  getPrometheusDetails(): Promise<AsyncResult<PrometheusDetails, Error>>;
   resolveAuthProxyUrl(): Promise<string>;
   resolveAuthProxyCa(): string;
   getApiTarget(isLongRunningRequest?: boolean): Promise<httpProxy.ServerOptions>;
@@ -50,6 +52,8 @@ export interface ClusterContextHandler {
   stopServer(): void;
 }
 
+const formatPrometheusPath = ({ service, namespace, port }: PrometheusService) => `${namespace}/services/${service}:${port}`;
+
 export class ContextHandler implements ClusterContextHandler {
   public readonly clusterUrl: UrlWithStringQuery;
   protected kubeAuthProxy?: KubeAuthProxy;
@@ -67,16 +71,20 @@ export class ContextHandler implements ClusterContextHandler {
     this.prometheus = preferences.prometheus;
   }
 
-  public async getPrometheusDetails(): Promise<PrometheusDetails> {
-    const service = await this.getPrometheusService();
-    const prometheusPath = this.ensurePrometheusPath(service);
-    const provider = this.ensurePrometheusProvider(service);
+  public async getPrometheusDetails(): Promise<AsyncResult<PrometheusDetails, Error>> {
+    const result = await this.getPrometheusService();
 
-    return { prometheusPath, provider };
-  }
+    if (!result.callWasSuccessful) {
+      return result;
+    }
 
-  protected ensurePrometheusPath({ service, namespace, port }: PrometheusService): string {
-    return `${namespace}/services/${service}:${port}`;
+    const prometheusPath = formatPrometheusPath(result.response);
+    const provider = this.ensurePrometheusProvider(result.response);
+
+    return {
+      callWasSuccessful: true,
+      response: { prometheusPath, provider },
+    };
   }
 
   protected ensurePrometheusProvider(service: PrometheusService): PrometheusProvider {
@@ -98,21 +106,45 @@ export class ContextHandler implements ClusterContextHandler {
     return this.dependencies.prometheusProviders.get();
   }
 
-  protected async getPrometheusService(): Promise<PrometheusService> {
+  private async getProxyKubeconfig(): Promise<AsyncResult<KubeConfig, Error>> {
+    try {
+      const proxyConfig = await this.cluster.getProxyKubeconfig();
+
+      return {
+        callWasSuccessful: true,
+        response: proxyConfig,
+      };
+    } catch (error) {
+      return {
+        callWasSuccessful: false,
+        error: error as Error,
+      };
+    }
+  }
+
+  protected async getPrometheusService(): Promise<AsyncResult<PrometheusService, Error>> {
     this.setupPrometheus(this.cluster.preferences);
 
     if (this.prometheus && this.prometheusProvider) {
       return {
-        kind: this.prometheusProvider,
-        namespace: this.prometheus.namespace,
-        service: this.prometheus.service,
-        port: this.prometheus.port,
+        callWasSuccessful: true,
+        response: {
+          kind: this.prometheusProvider,
+          namespace: this.prometheus.namespace,
+          service: this.prometheus.service,
+          port: this.prometheus.port,
+        },
       };
     }
 
     const providers = this.listPotentialProviders();
-    const proxyConfig = await this.cluster.getProxyKubeconfig();
-    const apiClient = this.dependencies.makeApiClient(proxyConfig, CoreV1Api);
+    const proxyConfigResult = await this.getProxyKubeconfig();
+
+    if (!proxyConfigResult.callWasSuccessful) {
+      return proxyConfigResult;
+    }
+
+    const apiClient = this.dependencies.makeApiClient(proxyConfigResult.response, CoreV1Api);
     const potentialServices = await Promise.allSettled(
       providers.map(provider => provider.getPrometheusService(apiClient)),
     );
@@ -126,12 +158,18 @@ export class ContextHandler implements ClusterContextHandler {
 
         case "fulfilled":
           if (res.value) {
-            return res.value;
+            return {
+              callWasSuccessful: true,
+              response: res.value,
+            };
           }
       }
     }
 
-    throw new Error("No Prometheus service found", { cause: errors });
+    return {
+      callWasSuccessful: false,
+      error: new Error("No Prometheus service found", { cause: errors }),
+    };
   }
 
   async resolveAuthProxyUrl(): Promise<string> {