diff --git a/.github/workflows/e2e-testing.yaml b/.github/workflows/e2e-testing.yaml
index 59d711f2..3c2b8135 100644
--- a/.github/workflows/e2e-testing.yaml
+++ b/.github/workflows/e2e-testing.yaml
@@ -8,6 +8,7 @@ on:
 jobs:
   test-e2e:
     strategy:
+      fail-fast: false
       matrix:
         os: [macos-latest, ubuntu-latest]
     runs-on: ${{ matrix.os }}
diff --git a/test/e2e/helpers/actions.ts b/test/e2e/helpers/actions.ts
index b9fabbcf..01ba2589 100644
--- a/test/e2e/helpers/actions.ts
+++ b/test/e2e/helpers/actions.ts
@@ -1,4 +1,12 @@
 import type { Workbench } from 'wdio-vscode-service'
+import { Key } from 'webdriverio'
+
+export async function clearInput(input: WebdriverIO.Element) {
+  // Focus the input, sometimes clicking doesn't work
+  await input.setValue('')
+  await browser.keys([Key.Ctrl, 'a'])
+  await browser.keys(Key.Backspace)
+}
 
 /**
  * Opens the Radicle view container in the sidebar, by clicking the radicle button in the
@@ -13,3 +21,13 @@ export async function openRadicleViewContainer(workbench: Workbench) {
 
   await radicleViewControl?.openView()
 }
+
+export async function closeRadicleViewContainer(workbench: Workbench) {
+  const activityBar = workbench.getActivityBar()
+  await activityBar.wait()
+
+  const radicleViewControl = await activityBar.getViewControl('Radicle')
+  await radicleViewControl?.wait()
+
+  await radicleViewControl?.closeView()
+}
diff --git a/test/e2e/helpers/assertions.ts b/test/e2e/helpers/assertions.ts
index 539d5c31..20cbcdee 100644
--- a/test/e2e/helpers/assertions.ts
+++ b/test/e2e/helpers/assertions.ts
@@ -1,5 +1,25 @@
 import { browser } from '@wdio/globals'
-import type { Workbench } from 'wdio-vscode-service'
+import type { OutputView, Workbench } from 'wdio-vscode-service'
+
+/**
+ * Asserts the Output Panel contains the expected text.
+ */
+export async function expectOutputToContain(outputView: OutputView, expected: string) {
+  await browser.waitUntil(
+    async () => {
+      /**
+       * The text in the Output Panel is split by newlines, which can be affected by the size
+       * of the window. To avoid this, we join the text into a single string.
+       */
+      const joinedText = (await outputView.getText()).join('')
+
+      return joinedText.includes(expected)
+    },
+    {
+      timeoutMsg: `expected the output text to contain "${expected}"`,
+    },
+  )
+}
 
 /**
  * Asserts that the CLI Commands and Patches sections are visible in the sidebar. This is
diff --git a/test/e2e/specs/onboarding.spec.ts b/test/e2e/specs/onboarding.spec.ts
index fff8b4e2..92cba08a 100644
--- a/test/e2e/specs/onboarding.spec.ts
+++ b/test/e2e/specs/onboarding.spec.ts
@@ -5,7 +5,7 @@ import { $, cd } from 'zx'
 import type * as VsCode from 'vscode'
 import isEqual from 'lodash/isEqual'
 import { expectStandardSidebarViewsToBeVisible } from '../helpers/assertions'
-import { openRadicleViewContainer } from '../helpers/actions'
+import { closeRadicleViewContainer, openRadicleViewContainer } from '../helpers/actions'
 import { getFirstWelcomeViewText } from '../helpers/queries'
 import { backupNodeHomePath, e2eTestDirPath, nodeHomePath } from '../constants/config'
 
@@ -16,6 +16,10 @@ describe('Onboarding Flow', () => {
     workbench = await browser.getWorkbench()
   })
 
+  after(async () => {
+    await closeRadicleViewContainer(workbench)
+  })
+
   describe('VS Code, *before* Radicle is installed,', () => {
     after(async () => {
       await $`mv ${backupNodeHomePath} ${nodeHomePath}`
diff --git a/test/e2e/specs/patch-details.spec.ts b/test/e2e/specs/patch-details.spec.ts
new file mode 100644
index 00000000..b16bd906
--- /dev/null
+++ b/test/e2e/specs/patch-details.spec.ts
@@ -0,0 +1,124 @@
+import type { WebView, Workbench } from 'wdio-vscode-service'
+import { $, browser } from '@wdio/globals'
+import { $ as zx } from 'zx'
+import { Key } from 'webdriverio'
+import { openRadicleViewContainer } from '../helpers/actions'
+
+const selectors = {
+  openPatchDetailsButton: 'aria/Open Patch Details',
+  changePathStatusButton: '[title="Change Patch Status"]',
+  draftRadioButton: 'aria/Draft',
+  stopEditingPatchStatusButton: '[title="Stop Editing Patch Status"]',
+  refreshPatchDataButton: '[title="Refresh Patch Data"]',
+  editPatchTitleButton: '[title="Edit Patch Title and Description"]',
+  patchTitleInput: 'aria/Patch Title:',
+  patchDescriptionInput: 'aria/Patch Description:',
+  savePatchTitleButton: '[title="Save Changes to Radicle (Ctrl + Enter)"]',
+  openPatchIcon: '.codicon-git-pull-request',
+  draftPatchIcon: '.codicon-git-pull-request-draft',
+  closedPatchIcon: '.codicon-git-pull-request-closed',
+}
+
+/**
+ * These tests are failing because the extension is not picking up httpd.
+ * An iteration of this suite with adjustments to run locally (with a pre-existing patch) has been
+ * tested (on macOS) and works as expected.
+ * Barring any unexpected behavior due to the CI environment, these tests *should* pass once the
+ * httpd issue is resolved.
+ *
+ * TODO: Figure out why the extension is not picking up httpd
+ */
+describe.skip('Patch Details', () => {
+  const patchTitle = 'feat: foo bar'
+  let workbench: Workbench
+
+  before(async () => {
+    workbench = await browser.getWorkbench()
+    await zx`git checkout -b branch-1`
+    await zx`echo "Hello, World!" > hello.txt`
+    await zx`git add .`
+    await zx`git commit -m "${patchTitle}"`
+    await zx`git push rad HEAD:refs/patches`
+    await openRadicleViewContainer(workbench)
+    await openPatchDetails(workbench, patchTitle)
+  })
+
+  describe("VS Code, when viewing a patch's details,", () => {
+    it('allows the user to edit the patch status', async () => {
+      const patchDetails = await switchToFirstWebView(workbench)
+
+      await $(selectors.changePathStatusButton).click()
+      await $(selectors.draftRadioButton).click()
+      await $(selectors.stopEditingPatchStatusButton).click()
+      await $(selectors.refreshPatchDataButton).moveTo()
+
+      await expect($(`header ${selectors.draftPatchIcon}`)).toBeDisplayed()
+
+      await patchDetails?.close()
+
+      await expect(
+        await (await findPatch(workbench, patchTitle))?.elem.$(selectors.draftPatchIcon),
+      ).toBeDisplayed()
+    })
+
+    it('allows the user to edit that patch title and description', async () => {
+      const patchDetails = await switchToFirstWebView(workbench)
+      await $(selectors.editPatchTitleButton).click()
+
+      const newTitle = 'feat: new foo bar'
+      const newDescription = 'foo bar baz'
+      await findAndFillInput(selectors.patchTitleInput, newTitle)
+      await findAndFillInput(selectors.patchDescriptionInput, newDescription)
+      await $(selectors.savePatchTitleButton).click()
+
+      await expect($(`p=${newTitle}`)).toBeDisplayed()
+
+      await expect($(`p=${newDescription}`)).toBeDisplayed()
+
+      await patchDetails?.close()
+
+      await expect(await findPatch(workbench, newTitle)).toBeDisplayed()
+    })
+  })
+})
+
+async function findAndFillInput(selector: string, value: string) {
+  await $(selector).click()
+  await browser.keys([Key.Ctrl, 'a'])
+  await browser.keys(value.split(''))
+}
+
+async function findPatch(workbench: Workbench, label: string) {
+  const sidebarView = workbench.getSideBar().getContent()
+  const patchesSection = await sidebarView.getSection('PATCHES')
+  const patch = await patchesSection.findItem(label)
+
+  return patch
+}
+
+async function openPatchDetails(workbench: Workbench, label: string) {
+  const patch = await findPatch(workbench, label)
+  if (!patch) {
+    return undefined
+  }
+
+  await patch.elem.moveTo()
+  await patch.elem.$(selectors.openPatchDetailsButton)?.click()
+
+  return patch
+}
+
+async function switchToFirstWebView(workbench: Workbench) {
+  let webviews: WebView[] = []
+  await browser.waitUntil(
+    async () => {
+      webviews = await workbench.getAllWebviews()
+
+      return webviews.length > 0
+    },
+    { timeoutMsg: 'no webviews found' },
+  )
+  await webviews[0]?.open()
+
+  return webviews[0]
+}
diff --git a/test/e2e/specs/settings.spec.ts b/test/e2e/specs/settings.spec.ts
new file mode 100644
index 00000000..d72000d2
--- /dev/null
+++ b/test/e2e/specs/settings.spec.ts
@@ -0,0 +1,216 @@
+import { browser } from '@wdio/globals'
+import type { OutputView, Setting, SettingsEditor, Workbench } from 'wdio-vscode-service'
+import isEqual from 'lodash/isEqual'
+import { Key } from 'webdriverio'
+import { $ } from 'zx'
+import { getFirstWelcomeViewText } from '../helpers/queries'
+import {
+  expectOutputToContain,
+  expectStandardSidebarViewsToBeVisible,
+} from '../helpers/assertions'
+import {
+  clearInput,
+  closeRadicleViewContainer,
+  openRadicleViewContainer,
+} from '../helpers/actions'
+import { nodeHomePath } from '../constants/config'
+
+const tempNodeHomePath = `${nodeHomePath}.temp`
+
+describe('Settings', () => {
+  let workbench: Workbench
+  let settings: SettingsEditor
+
+  before(async () => {
+    workbench = await browser.getWorkbench()
+    settings = await workbench.openSettings()
+    await openRadicleViewContainer(workbench)
+    await expectStandardSidebarViewsToBeVisible(workbench)
+  })
+
+  after(async () => {
+    await closeRadicleViewContainer(workbench)
+  })
+
+  describe('VS Code, when updating the "Path to Rad Binary" setting,', () => {
+    let pathToRadBinarySetting: Setting
+
+    before(async () => {
+      pathToRadBinarySetting = await settings.findSetting(
+        'Path To Rad Binary',
+        'Radicle',
+        'Advanced',
+      )
+    })
+
+    after(async () => {
+      await clearInput(await getSettingsSearchBox(settings))
+    })
+
+    afterEach(async () => {
+      await clearTextSetting(pathToRadBinarySetting)
+
+      await expectStandardSidebarViewsToBeVisible(workbench)
+    })
+
+    it('warns the user if the rad binary is not found', async () => {
+      await setTextSettingValue(pathToRadBinarySetting, '/tmp')
+
+      await expectRadBinaryNotFoundToBeVisible(workbench)
+    })
+
+    it('recognizes the rad binary when a valid path is specified', async () => {
+      await $`cp -r ${nodeHomePath} ${tempNodeHomePath}`
+
+      await setTextSettingValue(pathToRadBinarySetting, `/tmp`)
+
+      await expectRadBinaryNotFoundToBeVisible(workbench)
+
+      await setTextSettingValue(pathToRadBinarySetting, `${tempNodeHomePath}/bin/rad`)
+
+      await expectStandardSidebarViewsToBeVisible(workbench)
+
+      await $`rm -rf ${tempNodeHomePath}`
+    })
+
+    // TODO: Unskip when #172 covered by this case is fixed
+    it.skip('recognizes if the directory is created *after* the setting is set', async () => {
+      await setTextSettingValue(pathToRadBinarySetting, tempNodeHomePath)
+
+      await expectRadBinaryNotFoundToBeVisible(workbench)
+
+      await $`cp -r ${nodeHomePath} ${tempNodeHomePath}`
+
+      await expectStandardSidebarViewsToBeVisible(workbench)
+
+      await $`rm -rf ${tempNodeHomePath}`
+    })
+  })
+
+  /**
+   * These tests is skipped on Linux CI because the extension is having issues resolving the correct
+   * node home directory.
+   *
+   * TODO: Figure out why the extension is having issues resolving the correct node home directory
+   * on Linux CI.
+   */
+  // eslint-disable-next-line max-len
+  describe('VS Code, when updating the "Path to Radicle to Node Home" setting, @skipLinuxCI', () => {
+    let pathToNodeHomeSetting: Setting
+    let outputView: OutputView
+
+    before(async () => {
+      pathToNodeHomeSetting = await settings.findSetting(
+        'Path To Node Home',
+        'Radicle',
+        'Advanced',
+      )
+      await workbench.executeCommand('Show Everything Logged in the Output Panel')
+      outputView = await workbench.getBottomBar().openOutputView()
+    })
+
+    after(async () => {
+      await clearInput(await getSettingsSearchBox(settings))
+    })
+
+    afterEach(async () => {
+      await outputView.clearText()
+      await clearTextSetting(pathToNodeHomeSetting)
+
+      await expectRadicleIdentityToBeFound(outputView)
+    })
+
+    it('logs an error in the output console if the path is invalid', async () => {
+      await outputView.clearText()
+
+      await setTextSettingValue(pathToNodeHomeSetting, '/tmp')
+
+      await expectRadicleProfileNotToBeFound(outputView)
+    })
+
+    it('recognizes when a valid path is specified', async () => {
+      await $`cp -r ${nodeHomePath} ${tempNodeHomePath}`
+      await outputView.clearText()
+
+      await setTextSettingValue(pathToNodeHomeSetting, tempNodeHomePath)
+
+      await expectRadicleIdentityToBeFound(outputView)
+
+      await $`rm -rf ${tempNodeHomePath}`
+    })
+
+    // TODO: Unskip when #172 covered by this case is fixed
+    it.skip('recognizes if the directory is created *after* the setting is set', async () => {
+      await outputView.clearText()
+
+      await setTextSettingValue(pathToNodeHomeSetting, tempNodeHomePath)
+
+      await expectRadicleProfileNotToBeFound(outputView)
+
+      await $`cp -r ${nodeHomePath} ${tempNodeHomePath}`
+
+      await expectRadicleIdentityToBeFound(outputView)
+
+      await $`rm -rf ${tempNodeHomePath}`
+    })
+  })
+})
+
+async function expectRadBinaryNotFoundToBeVisible(workbench: Workbench) {
+  await browser.waitUntil(
+    async () => {
+      const welcomeText = await getFirstWelcomeViewText(workbench)
+
+      return isEqual(welcomeText, [
+        /* eslint-disable max-len */
+        'Failed resolving the Radicle CLI binary.',
+        "Please ensure it is installed on your machine and either that it is globally accessible in the shell as `rad` or that its path is correctly defined in the extension's settings.",
+        "Please expect the extention's capabilities to remain severely limited until this issue is resolved.",
+        /* eslint-enable max-len */
+      ])
+    },
+    { timeoutMsg: 'expected the rad binary not found message to be visible' },
+  )
+}
+
+async function expectRadicleIdentityToBeFound(outputView: OutputView) {
+  await expectOutputToContain(outputView, 'Using already unsealed Radicle identity')
+}
+
+async function expectRadicleProfileNotToBeFound(outputView: OutputView) {
+  await expectOutputToContain(outputView, '✗ Error: Radicle profile not found in')
+}
+
+/**
+ * Workaround to get the value of a `TextSetting`.
+ * The `getValue` method of a `TextSetting` seems to be wrongly implemented and returns null.
+ */
+async function getTextSettingValue(setting: Setting) {
+  return await setting.textSetting$.getValue()
+}
+
+async function setTextSettingValue(setting: Setting, value: string) {
+  await clearTextSetting(setting)
+  await setting.setValue(value)
+}
+
+async function clearTextSetting(setting: Setting) {
+  /**
+   * `.setValue('')` updates the value of the input but does not trigger an
+   * update in the extension. Not sure if this is a bug in the extension, vscode, or
+   * webdriverio.
+   *
+   * The following is a workaround that does trigger an update in the extension.
+   */
+  if ((await getTextSettingValue(setting)) === '') {
+    return
+  }
+
+  await setting.textSetting$.click()
+  await browser.keys([Key.Ctrl, 'a'])
+  await browser.keys(Key.Backspace)
+}
+
+async function getSettingsSearchBox(settings: SettingsEditor) {
+  return await settings.elem.$(settings.locatorMap.Editor['inputArea'] as string)
+}
diff --git a/test/e2e/wdio.conf.ts b/test/e2e/wdio.conf.ts
index d95a3414..d7372cd6 100644
--- a/test/e2e/wdio.conf.ts
+++ b/test/e2e/wdio.conf.ts
@@ -1,4 +1,4 @@
-import path from 'node:path'
+import path, { sep } from 'node:path'
 import { $ } from 'zx'
 import type { Options } from '@wdio/types'
 import {
@@ -18,6 +18,26 @@ if (!process.env['CI']) {
 // eslint-disable-next-line @typescript-eslint/no-unsafe-member-access
 const vscodeVersion = (packageJson.engines.vscode as string).replace(/^\^/, '')
 
+const skipTestsGrep = []
+
+switch (process.platform) {
+  case 'darwin':
+    skipTestsGrep.push('@skipMacOSCI')
+    break
+  case 'linux':
+    skipTestsGrep.push('@skipLinuxCI')
+    break
+}
+
+const orderedSpecPaths = [
+  './specs/onboarding.spec.ts',
+  './specs/settings.spec.ts',
+  './specs/patch-details.spec.ts',
+].map((specPath) => specPath.replace('/', sep))
+const specsToExcludeFromGlob = orderedSpecPaths.map((specPath) =>
+  specPath.split(sep).at(-1)?.replace('.spec.ts', ''),
+)
+
 // TODO: Bump webdriverio to v9 once wdio-vscode-service supports it
 // Relevant PR: https://github.com/webdriverio-community/wdio-vscode-service/pull/130
 // Relevant Issue: https://github.com/webdriverio-community/wdio-vscode-service/issues/140
@@ -29,7 +49,7 @@ export const config: Options.Testrunner = {
       transpileOnly: true,
     },
   },
-  specs: ['./specs/**/*.ts'],
+  specs: [orderedSpecPaths, `./specs/**/!(${specsToExcludeFromGlob.join('|')}).spec.ts`],
   maxInstances: 10,
   capabilities: [
     {
@@ -50,13 +70,15 @@ export const config: Options.Testrunner = {
     },
   ],
   logLevel: 'warn',
-  waitforTimeout: 10000,
+  waitforTimeout: 20000,
   services: [['vscode', { cachePath: path.join(rootDirPath, 'node_modules/.cache/wdio') }]],
   framework: 'mocha',
   reporters: ['spec'],
   mochaOpts: {
     ui: 'bdd',
     timeout: 60000,
+    grep: skipTestsGrep.length > 0 ? skipTestsGrep.join('|') : undefined,
+    invert: true,
   },
   onPrepare: async () => {
     await $`mkdir -p ${path.join(rootDirPath, 'node_modules/.cache/wdio')}`