diff --git a/packages/gatsby-cli/src/structured-errors/error-map.ts b/packages/gatsby-cli/src/structured-errors/error-map.ts
index e78eaf62ac7d5..787bee8595e7a 100644
--- a/packages/gatsby-cli/src/structured-errors/error-map.ts
+++ b/packages/gatsby-cli/src/structured-errors/error-map.ts
@@ -370,6 +370,13 @@ const errors = {
     level: Level.ERROR,
     category: ErrorCategory.USER,
   },
+  "10127": {
+    text: (context): string =>
+      `Your "${context.configName}.ts" file failed to compile to "${context.configName}.js. Please run "gatsby clean" and try again.\n\nIf the issue persists, please open an issue with a reproduction at https://github.com/gatsbyjs/gatsby/issues/new for more help."`,
+    type: Type.CONFIG,
+    level: Level.ERROR,
+    category: ErrorCategory.USER,
+  },
   "10226": {
     text: (context): string =>
       [
diff --git a/packages/gatsby/src/bootstrap/__mocks__/get-config/compiled-dir/compiled/gatsby-config.js b/packages/gatsby/src/bootstrap/__mocks__/get-config/compiled-dir/compiled/gatsby-config.js
new file mode 100644
index 0000000000000..902eb91623cdd
--- /dev/null
+++ b/packages/gatsby/src/bootstrap/__mocks__/get-config/compiled-dir/compiled/gatsby-config.js
@@ -0,0 +1,7 @@
+module.exports = {
+  siteMetadata: {
+    title: `compiled`,
+    siteUrl: `https://www.yourdomain.tld`,
+  },
+  plugins: [],
+}
diff --git a/packages/gatsby/src/bootstrap/__mocks__/get-config/gatsby-config.js b/packages/gatsby/src/bootstrap/__mocks__/get-config/gatsby-config.js
new file mode 100644
index 0000000000000..d2d39c7540947
--- /dev/null
+++ b/packages/gatsby/src/bootstrap/__mocks__/get-config/gatsby-config.js
@@ -0,0 +1,7 @@
+module.exports = {
+  siteMetadata: {
+    title: `uncompiled`,
+    siteUrl: `https://www.yourdomain.tld`,
+  },
+  plugins: [],
+}
diff --git a/packages/gatsby/src/bootstrap/__mocks__/get-config/near-match-dir/gatsby-confi.js b/packages/gatsby/src/bootstrap/__mocks__/get-config/near-match-dir/gatsby-confi.js
new file mode 100644
index 0000000000000..1afabc2b4caf8
--- /dev/null
+++ b/packages/gatsby/src/bootstrap/__mocks__/get-config/near-match-dir/gatsby-confi.js
@@ -0,0 +1,7 @@
+module.exports = {
+  siteMetadata: {
+    title: `near-match`,
+    siteUrl: `https://www.yourdomain.tld`,
+  },
+  plugins: [],
+}
diff --git a/packages/gatsby/src/bootstrap/__mocks__/get-config/src-dir/src/gatsby-config.js b/packages/gatsby/src/bootstrap/__mocks__/get-config/src-dir/src/gatsby-config.js
new file mode 100644
index 0000000000000..1b131c74660d2
--- /dev/null
+++ b/packages/gatsby/src/bootstrap/__mocks__/get-config/src-dir/src/gatsby-config.js
@@ -0,0 +1,7 @@
+module.exports = {
+  siteMetadata: {
+    title: `in-src`,
+    siteUrl: `https://www.yourdomain.tld`,
+  },
+  plugins: [],
+}
diff --git a/packages/gatsby/src/bootstrap/__mocks__/get-config/ts-dir/gatsby-config.ts b/packages/gatsby/src/bootstrap/__mocks__/get-config/ts-dir/gatsby-config.ts
new file mode 100644
index 0000000000000..88954db73357d
--- /dev/null
+++ b/packages/gatsby/src/bootstrap/__mocks__/get-config/ts-dir/gatsby-config.ts
@@ -0,0 +1,11 @@
+import type { GatsbyConfig } from "gatsby"
+
+const config: GatsbyConfig = {
+  siteMetadata: {
+    title: `ts`,
+    siteUrl: `https://www.yourdomain.tld`,
+  },
+  plugins: [],
+}
+
+export default config
diff --git a/packages/gatsby/src/bootstrap/__mocks__/get-config/user-require-dir/compiled/gatsby-config.js b/packages/gatsby/src/bootstrap/__mocks__/get-config/user-require-dir/compiled/gatsby-config.js
new file mode 100644
index 0000000000000..ea1e68c533fb5
--- /dev/null
+++ b/packages/gatsby/src/bootstrap/__mocks__/get-config/user-require-dir/compiled/gatsby-config.js
@@ -0,0 +1,9 @@
+const something = require(`some-place-that-does-not-exist`)
+
+module.exports = {
+  siteMetadata: {
+    title: `user-require-error`,
+    siteUrl: `https://www.yourdomain.tld`,
+  },
+  plugins: [],
+}
diff --git a/packages/gatsby/src/bootstrap/__tests__/get-config-file.ts b/packages/gatsby/src/bootstrap/__tests__/get-config-file.ts
new file mode 100644
index 0000000000000..8ab13985538d0
--- /dev/null
+++ b/packages/gatsby/src/bootstrap/__tests__/get-config-file.ts
@@ -0,0 +1,164 @@
+import path from "path"
+import { isNearMatch, getConfigFile } from "../get-config-file"
+import { testRequireError } from "../../utils/test-require-error"
+import reporter from "gatsby-cli/lib/reporter"
+
+jest.mock(`path`, () => {
+  const actual = jest.requireActual(`path`)
+  return {
+    ...actual,
+    join: jest.fn((...arg) => actual.join(...arg)),
+  }
+})
+
+jest.mock(`../../utils/test-require-error`, () => {
+  return {
+    testRequireError: jest.fn(),
+  }
+})
+
+jest.mock(`../../utils/parcel/compile-gatsby-files`, () => {
+  const actual = jest.requireActual(`../../utils/parcel/compile-gatsby-files`)
+  return {
+    ...actual,
+    COMPILED_CACHE_DIR: `compiled`, // .cache is git ignored
+  }
+})
+
+jest.mock(`gatsby-cli/lib/reporter`, () => {
+  return {
+    panic: jest.fn(),
+  }
+})
+
+const pathJoinMock = path.join as jest.MockedFunction<typeof path.join>
+
+const testRequireErrorMock = testRequireError as jest.MockedFunction<
+  typeof testRequireError
+>
+
+const reporterPanicMock = reporter.panic as jest.MockedFunction<
+  typeof reporter.panic
+>
+
+describe(`isNearMatch`, () => {
+  it(`should NOT find a near match if file name is undefined`, () => {
+    const nearMatchA = isNearMatch(undefined, `gatsby-config`, 1)
+    expect(nearMatchA).toBeFalse()
+  })
+
+  it(`should calculate near matches based on distance`, () => {
+    const nearMatchA = isNearMatch(`gatsby-config`, `gatsby-conf`, 2)
+    const nearMatchB = isNearMatch(`gatsby-config`, `gatsby-configur`, 2)
+    expect(nearMatchA).toBeTrue()
+    expect(nearMatchB).toBeTrue()
+  })
+})
+
+// Separate config directories so cases can be tested separately
+const dir = path.resolve(__dirname, `../__mocks__/get-config`)
+const compiledDir = `${dir}/compiled-dir`
+const userRequireDir = `${dir}/user-require-dir`
+const tsDir = `${dir}/ts-dir`
+const nearMatchDir = `${dir}/near-match-dir`
+const srcDir = `${dir}/src-dir`
+
+describe(`getConfigFile`, () => {
+  beforeEach(() => {
+    reporterPanicMock.mockClear()
+  })
+
+  it(`should get an uncompiled gatsby-config.js`, async () => {
+    const { configModule, configFilePath } = await getConfigFile(
+      dir,
+      `gatsby-config`
+    )
+    expect(configFilePath).toBe(path.join(dir, `gatsby-config.js`))
+    expect(configModule.siteMetadata.title).toBe(`uncompiled`)
+  })
+
+  it(`should get a compiled gatsby-config.js`, async () => {
+    const { configModule, configFilePath } = await getConfigFile(
+      compiledDir,
+      `gatsby-config`
+    )
+    expect(configFilePath).toBe(
+      path.join(compiledDir, `compiled`, `gatsby-config.js`)
+    )
+    expect(configModule.siteMetadata.title).toBe(`compiled`)
+  })
+
+  it(`should handle user require errors found in compiled gatsby-config.js`, async () => {
+    await getConfigFile(userRequireDir, `gatsby-config`)
+
+    expect(reporterPanicMock).toBeCalledWith({
+      id: `11902`,
+      error: expect.toBeObject(),
+      context: {
+        configName: `gatsby-config`,
+        message: expect.toBeString(),
+      },
+    })
+  })
+
+  it(`should handle non-require errors`, async () => {
+    testRequireErrorMock.mockImplementationOnce(() => false)
+
+    await getConfigFile(nearMatchDir, `gatsby-config`)
+
+    expect(reporterPanicMock).toBeCalledWith({
+      id: `10123`,
+      error: expect.toBeObject(),
+      context: {
+        configName: `gatsby-config`,
+        message: expect.toBeString(),
+      },
+    })
+  })
+
+  it(`should handle case where gatsby-config.ts exists but no compiled gatsby-config.js exists`, async () => {
+    // Force outer and inner errors so we can hit the code path that checks if gatsby-config.ts exists
+    pathJoinMock
+      .mockImplementationOnce(() => `force-outer-error`)
+      .mockImplementationOnce(() => `force-inner-error`)
+    testRequireErrorMock.mockImplementationOnce(() => true)
+
+    await getConfigFile(tsDir, `gatsby-config`)
+
+    expect(reporterPanicMock).toBeCalledWith({
+      id: `10127`,
+      error: expect.toBeObject(),
+      context: {
+        configName: `gatsby-config`,
+      },
+    })
+  })
+
+  it(`should handle near matches`, async () => {
+    testRequireErrorMock.mockImplementationOnce(() => true)
+
+    await getConfigFile(nearMatchDir, `gatsby-config`)
+
+    expect(reporterPanicMock).toBeCalledWith({
+      id: `10124`,
+      error: expect.toBeObject(),
+      context: {
+        configName: `gatsby-config`,
+        nearMatch: `gatsby-confi.js`,
+      },
+    })
+  })
+
+  it(`should handle gatsby config incorrectly located in src dir`, async () => {
+    testRequireErrorMock.mockImplementationOnce(() => true)
+
+    await getConfigFile(srcDir, `gatsby-config`)
+
+    expect(reporterPanicMock).toBeCalledWith({
+      id: `10125`,
+      context: {
+        configName: `gatsby-config`,
+      },
+    })
+  })
+})
diff --git a/packages/gatsby/src/bootstrap/get-config-file.ts b/packages/gatsby/src/bootstrap/get-config-file.ts
index dcca8f43cf2dd..a04a10f3232f8 100644
--- a/packages/gatsby/src/bootstrap/get-config-file.ts
+++ b/packages/gatsby/src/bootstrap/get-config-file.ts
@@ -6,7 +6,7 @@ import path from "path"
 import { sync as existsSync } from "fs-exists-cached"
 import { COMPILED_CACHE_DIR } from "../utils/parcel/compile-gatsby-files"
 
-function isNearMatch(
+export function isNearMatch(
   fileName: string | undefined,
   configName: string,
   distance: number
@@ -27,8 +27,8 @@ export async function getConfigFile(
   let configFilePath = ``
   let configModule: any
 
+  // Attempt to find compiled gatsby-config.js in .cache/compiled/gatsby-config.js
   try {
-    // Try .cache/compiled/gatsby-config first
     configPath = path.join(`${siteDirectory}/${COMPILED_CACHE_DIR}`, configName)
     configFilePath = require.resolve(configPath)
     configModule = require(configFilePath)
@@ -42,6 +42,7 @@ export async function getConfigFile(
     const isThisFileRequireError =
       outerError?.requireStack?.[0]?.includes(`get-config-file`) ?? true
 
+    // User's module require error inside gatsby-config.js
     if (!(isModuleNotFoundError && isThisFileRequireError)) {
       report.panic({
         id: `11902`,
@@ -53,19 +54,14 @@ export async function getConfigFile(
       })
     }
 
-    // Fallback to regular rootDir gatsby-config
+    // Attempt to find uncompiled gatsby-config.js in root dir
     configPath = path.join(siteDirectory, configName)
+
     try {
       configFilePath = require.resolve(configPath)
       configModule = require(configFilePath)
     } catch (innerError) {
-      // Only then hard fail
-      const nearMatch = await fs.readdir(siteDirectory).then(files =>
-        files.find(file => {
-          const fileName = file.split(siteDirectory).pop()
-          return isNearMatch(fileName, configName, distance)
-        })
-      )
+      // Some other error that is not a require error
       if (!testRequireError(configPath, innerError)) {
         report.panic({
           id: `10123`,
@@ -75,7 +71,43 @@ export async function getConfigFile(
             message: innerError.message,
           },
         })
-      } else if (nearMatch) {
+      }
+
+      const files = await fs.readdir(siteDirectory)
+
+      let tsConfig = false
+      let nearMatch = ``
+
+      for (const file of files) {
+        if (tsConfig || nearMatch) {
+          break
+        }
+
+        const { name, ext } = path.parse(file)
+
+        if (name === configName && ext === `.ts`) {
+          tsConfig = true
+          break
+        }
+
+        if (isNearMatch(name, configName, distance)) {
+          nearMatch = file
+        }
+      }
+
+      // gatsby-config.ts exists but compiled gatsby-config.js does not
+      if (tsConfig) {
+        report.panic({
+          id: `10127`,
+          error: innerError,
+          context: {
+            configName,
+          },
+        })
+      }
+
+      // gatsby-config is misnamed
+      if (nearMatch) {
         report.panic({
           id: `10124`,
           error: innerError,
@@ -84,9 +116,10 @@ export async function getConfigFile(
             nearMatch,
           },
         })
-      } else if (
-        existsSync(path.join(siteDirectory, `src`, configName + `.js`))
-      ) {
+      }
+
+      // gatsby-config.js is incorrectly located in src/gatsby-config.js
+      if (existsSync(path.join(siteDirectory, `src`, configName + `.js`))) {
         report.panic({
           id: `10125`,
           context: {