diff --git a/packages/edge-bundler/node/bundler.test.ts b/packages/edge-bundler/node/bundler.test.ts
index 15fc9c6659..a1bfd32ec6 100644
--- a/packages/edge-bundler/node/bundler.test.ts
+++ b/packages/edge-bundler/node/bundler.test.ts
@@ -1,16 +1,15 @@
 import { Buffer } from 'buffer'
-import { execSync } from 'node:child_process'
 import { access, readdir, readFile, rm, writeFile } from 'fs/promises'
 import { join, resolve } from 'path'
 import process from 'process'
 import { pathToFileURL } from 'url'
 
-import { lt } from 'semver'
+import { gte, lt } from 'semver'
 import tmp from 'tmp-promise'
 import { test, expect, vi, describe } from 'vitest'
 
 import { importMapSpecifier } from '../shared/consts.js'
-import { runESZIP, runTarball, useFixture } from '../test/util.js'
+import { denoVersion, runESZIP, runTarball, useFixture } from '../test/util.js'
 
 import { BundleError } from './bundle_error.js'
 import { bundle, BundleOptions } from './bundler.js'
@@ -599,7 +598,7 @@ test('Loads npm modules in a monorepo setup', async () => {
   await rm(vendorDirectory.path, { force: true, recursive: true })
 })
 
-test('Loads JSON modules', async () => {
+test('Loads JSON modules with `with` attribute', async () => {
   const { basePath, cleanup, distPath } = await useFixture('imports_json')
   const sourceDirectory = join(basePath, 'functions')
   const declarations: Declaration[] = [
@@ -626,6 +625,45 @@ test('Loads JSON modules', async () => {
   await rm(vendorDirectory.path, { force: true, recursive: true })
 })
 
+// We can't run this on versions above 2.0.0 because the bundling will fail
+// entirely, and what we're asserting here is that we emit a system log when
+// import assertions are detected on successful builds. Also, running it on
+// earlier versions won't work either, since those won't even show a warning.
+test.skipIf(lt(denoVersion, '1.46.3') || gte(denoVersion, '2.0.0'))(
+  'Emits a system log when import assertions are used',
+  async () => {
+    const { basePath, cleanup, distPath } = await useFixture('with_import_assert')
+    const sourceDirectory = join(basePath, 'functions')
+    const declarations: Declaration[] = [
+      {
+        function: 'func1',
+        path: '/func1',
+      },
+    ]
+    const vendorDirectory = await tmp.dir()
+    const systemLogger = vi.fn()
+
+    await bundle([sourceDirectory], distPath, declarations, {
+      basePath,
+      systemLogger,
+      vendorDirectory: vendorDirectory.path,
+    })
+
+    const manifestFile = await readFile(resolve(distPath, 'manifest.json'), 'utf8')
+    const manifest = JSON.parse(manifestFile)
+    const bundlePath = join(distPath, manifest.bundles[0].asset)
+    const { func1 } = await runESZIP(bundlePath, vendorDirectory.path)
+
+    expect(func1).toBe(`{"foo":"bar"}`)
+    expect(systemLogger).toHaveBeenCalledWith(
+      `Edge function uses import assertions: ${join(sourceDirectory, 'func1.ts')}`,
+    )
+
+    await cleanup()
+    await rm(vendorDirectory.path, { force: true, recursive: true })
+  },
+)
+
 test('Supports TSX and process.env', async () => {
   const { basePath, cleanup, distPath } = await useFixture('tsx')
   const sourceDirectory = join(basePath, 'functions')
@@ -694,8 +732,6 @@ test('Loads edge functions from the Frameworks API', async () => {
   await cleanup()
 })
 
-const denoVersion = execSync('deno eval --no-lock "console.log(Deno.version.deno)"').toString()
-
 describe.skipIf(lt(denoVersion, '2.4.2'))(
   'Produces a tarball bundle',
   () => {
diff --git a/packages/edge-bundler/node/config.ts b/packages/edge-bundler/node/config.ts
index cc64c1df12..df76405915 100644
--- a/packages/edge-bundler/node/config.ts
+++ b/packages/edge-bundler/node/config.ts
@@ -96,11 +96,12 @@ export const getFunctionConfig = async ({
   // with the extractor.
   const collector = await tmp.file()
 
+  // Retrieving the version of Deno.
+  const version = new SemVer((await deno.getBinaryVersion((await deno.getBinaryPath({ silent: true })).path)) || '')
+
   // The extractor will use its exit code to signal different error scenarios,
   // based on the list of exit codes we send as an argument. We then capture
   // the exit code to know exactly what happened and guide people accordingly.
-  const version = new SemVer((await deno.getBinaryVersion((await deno.getBinaryPath({ silent: true })).path)) || '')
-
   const { exitCode, stderr, stdout } = await deno.run(
     [
       'run',
@@ -121,6 +122,10 @@ export const getFunctionConfig = async ({
     { rejectOnExitCode: false },
   )
 
+  if (stderr.includes('Import assertions are deprecated')) {
+    log.system(`Edge function uses import assertions: ${func.path}`)
+  }
+
   if (exitCode !== ConfigExitCode.Success) {
     handleConfigError(func, exitCode, stderr, log)
 
diff --git a/packages/edge-bundler/test/fixtures/with_import_assert/functions/dict.json b/packages/edge-bundler/test/fixtures/with_import_assert/functions/dict.json
new file mode 100644
index 0000000000..b42f309e7a
--- /dev/null
+++ b/packages/edge-bundler/test/fixtures/with_import_assert/functions/dict.json
@@ -0,0 +1,3 @@
+{
+  "foo": "bar"
+}
\ No newline at end of file
diff --git a/packages/edge-bundler/test/fixtures/with_import_assert/functions/func1.ts b/packages/edge-bundler/test/fixtures/with_import_assert/functions/func1.ts
new file mode 100644
index 0000000000..1471989aaf
--- /dev/null
+++ b/packages/edge-bundler/test/fixtures/with_import_assert/functions/func1.ts
@@ -0,0 +1,4 @@
+import dict from './dict.json' assert { type: "json" }
+
+
+export default async () => Response.json(dict)
diff --git a/packages/edge-bundler/test/util.ts b/packages/edge-bundler/test/util.ts
index 0b54dc55d1..e0e56c643d 100644
--- a/packages/edge-bundler/test/util.ts
+++ b/packages/edge-bundler/test/util.ts
@@ -1,7 +1,8 @@
-import { promises as fs } from 'fs'
-import { join, resolve } from 'path'
-import { stderr, stdout } from 'process'
-import { fileURLToPath, pathToFileURL } from 'url'
+import { execSync } from 'node:child_process'
+import { promises as fs } from 'node:fs'
+import { join, resolve } from 'node:path'
+import { stderr, stdout } from 'node:process'
+import { fileURLToPath, pathToFileURL } from 'node:url'
 
 import cpy from 'cpy'
 import { execa } from 'execa'
@@ -169,3 +170,5 @@ export const runTarball = async (tarballPath: string) => {
 
   return JSON.parse(result.stdout)
 }
+
+export const denoVersion = execSync('deno eval --no-lock "console.log(Deno.version.deno)"').toString()