diff --git a/.changeset/tiny-ties-destroy.md b/.changeset/tiny-ties-destroy.md
new file mode 100644
index 000000000000..2bc3f04de19f
--- /dev/null
+++ b/.changeset/tiny-ties-destroy.md
@@ -0,0 +1,5 @@
+---
+"wrangler": patch
+---
+
+polish: improved visualization of the deprecation messages between serious and warnings with emojis. This also improves the delineation between messages.
diff --git a/packages/wrangler/src/__tests__/configuration.test.ts b/packages/wrangler/src/__tests__/configuration.test.ts
index 06ca09e454f8..5b3ea1049c64 100644
--- a/packages/wrangler/src/__tests__/configuration.test.ts
+++ b/packages/wrangler/src/__tests__/configuration.test.ts
@@ -322,7 +322,7 @@ describe("normalizeAndValidateConfig()", () => {
         `);
         expect(diagnostics.renderErrors()).toMatchInlineSnapshot(`
           "Processing wrangler configuration:
-            - DEPRECATION: \\"site.entry-point\\":
+            - 🚨 NO LONGER SUPPORTED: \\"site.entry-point\\":
               The \`site.entry-point\` config field is no longer used.
               The entry-point should be specified via the command line or the \`main\` config field."
         `);
@@ -532,12 +532,12 @@ describe("normalizeAndValidateConfig()", () => {
         expect(diagnostics.hasErrors()).toBe(false);
         expect(diagnostics.hasWarnings()).toBe(true);
         expect(diagnostics.renderWarnings()).toMatchInlineSnapshot(`
-            "Processing wrangler configuration:
-              - DEPRECATION: \\"type\\":
-                DO NOT USE THIS. Most common features now work out of the box with wrangler, including modules, jsx, typescript, etc. If you need anything more, use a custom build.
-              - DEPRECATION: \\"webpack_config\\":
-                DO NOT USE THIS. Most common features now work out of the box with wrangler, including modules, jsx, typescript, etc. If you need anything more, use a custom build."
-          `);
+          "Processing wrangler configuration:
+            - 🦺 DEPRECATION: \\"type\\":
+              DO NOT USE THIS. Most common features now work out of the box with wrangler, including modules, jsx, typescript, etc. If you need anything more, use a custom build.
+            - 🦺 DEPRECATION: \\"webpack_config\\":
+              DO NOT USE THIS. Most common features now work out of the box with wrangler, including modules, jsx, typescript, etc. If you need anything more, use a custom build."
+        `);
       });
     });
   });
@@ -699,15 +699,15 @@ describe("normalizeAndValidateConfig()", () => {
       expect(normalizePath(diagnostics.renderWarnings()))
         .toMatchInlineSnapshot(`
         "Processing project/wrangler.toml configuration:
-          - DEPRECATION: \\"build.upload.format\\":
+          - 🦺 DEPRECATION: \\"build.upload.format\\":
             The format is inferred automatically from the code.
-          - DEPRECATION: \\"build.upload.main\\":
+          - 🦺 DEPRECATION: \\"build.upload.main\\":
             Delete the \`build.upload.main\` and \`build.upload.dir\` fields.
             Then add the top level \`main\` field to your configuration file:
             \`\`\`
             main = \\"src/index.ts\\"
             \`\`\`
-          - DEPRECATION: \\"build.upload.dir\\":
+          - 🦺 DEPRECATION: \\"build.upload.dir\\":
             Use the top level \\"main\\" field or a command-line argument to specify the entry-point for the Worker.
           - DEPRECATION: The \`build.upload.rules\` config field is no longer used, the rules should be specified via the \`rules\` config field. Delete the \`build.upload\` field from the configuration file, and add this:
             \`\`\`
@@ -1448,19 +1448,19 @@ describe("normalizeAndValidateConfig()", () => {
         expect(diagnostics.hasErrors()).toBe(false);
         expect(diagnostics.hasWarnings()).toBe(true);
         expect(diagnostics.renderWarnings()).toMatchInlineSnapshot(`
-            "Processing wrangler configuration:
-              - DEPRECATION: \\"zone_id\\":
-                This is unnecessary since we can deduce this from routes directly.
-              - DEPRECATION: \\"experimental_services\\":
-                The \\"experimental_services\\" field is no longer supported. Instead, use [[unsafe.bindings]] to enable experimental features. Add this to your wrangler.toml:
-                \`\`\`
-                [[unsafe.bindings]]
-                name = \\"NAME\\"
-                type = \\"service\\"
-                service = \\"SERVICE\\"
-                environment = \\"ENV\\"
-                \`\`\`"
-          `);
+          "Processing wrangler configuration:
+            - 🦺 DEPRECATION: \\"zone_id\\":
+              This is unnecessary since we can deduce this from routes directly.
+            - 🦺 DEPRECATION: \\"experimental_services\\":
+              The \\"experimental_services\\" field is no longer supported. Instead, use [[unsafe.bindings]] to enable experimental features. Add this to your wrangler.toml:
+              \`\`\`
+              [[unsafe.bindings]]
+              name = \\"NAME\\"
+              type = \\"service\\"
+              service = \\"SERVICE\\"
+              environment = \\"ENV\\"
+              \`\`\`"
+        `);
       });
     });
 
@@ -2615,9 +2615,9 @@ describe("normalizeAndValidateConfig()", () => {
           "Processing wrangler configuration:
 
             - \\"env.ENV1\\" environment configuration
-              - DEPRECATION: \\"zone_id\\":
+              - 🦺 DEPRECATION: \\"zone_id\\":
                 This is unnecessary since we can deduce this from routes directly.
-              - DEPRECATION: \\"experimental_services\\":
+              - 🦺 DEPRECATION: \\"experimental_services\\":
                 The \\"experimental_services\\" field is no longer supported. Instead, use [[unsafe.bindings]] to enable experimental features. Add this to your wrangler.toml:
                 \`\`\`
                 [[unsafe.bindings]]
diff --git a/packages/wrangler/src/__tests__/index.test.ts b/packages/wrangler/src/__tests__/index.test.ts
index 6a01a8f8d1b0..d8dd2d1c3970 100644
--- a/packages/wrangler/src/__tests__/index.test.ts
+++ b/packages/wrangler/src/__tests__/index.test.ts
@@ -845,14 +845,14 @@ describe("wrangler", () => {
     it("should throw an error if the deprecated command is used with positional arguments", async () => {
       await expect(runWrangler("preview GET")).rejects
         .toThrowErrorMatchingInlineSnapshot(`
-              "DEPRECATION:
+              "🦺 DEPRECATION:
               The \`wrangler preview\` command has been deprecated.
               Try using \`wrangler dev\` to to try out a worker during development.
               "
             `);
       await expect(runWrangler(`preview GET "SomeBody"`)).rejects
         .toThrowErrorMatchingInlineSnapshot(`
-              "DEPRECATION:
+              "🦺 DEPRECATION:
               The \`wrangler preview\` command has been deprecated.
               Try using \`wrangler dev\` to to try out a worker during development.
               "
@@ -970,7 +970,7 @@ describe("wrangler", () => {
     it("should print a deprecation message for 'generate'", async () => {
       await runWrangler("generate").catch((err) => {
         expect(err.message).toMatchInlineSnapshot(`
-          "DEPRECATION:
+          "🦺 DEPRECATION:
           \`wrangler generate\` has been deprecated, please refer to https://github.com/cloudflare/wrangler2/blob/main/docs/deprecations.md#generate for alternatives"
         `);
       });
@@ -978,7 +978,7 @@ describe("wrangler", () => {
     it("should print a deprecation message for 'build'", async () => {
       await runWrangler("build").catch((err) => {
         expect(err.message).toMatchInlineSnapshot(`
-          "DEPRECATION:
+          "🦺 DEPRECATION:
           \`wrangler build\` has been deprecated, please refer to https://github.com/cloudflare/wrangler2/blob/main/docs/deprecations.md#build for alternatives"
         `);
       });
diff --git a/packages/wrangler/src/__tests__/publish.test.ts b/packages/wrangler/src/__tests__/publish.test.ts
index 87079fd3642f..a5ff5ac24b57 100644
--- a/packages/wrangler/src/__tests__/publish.test.ts
+++ b/packages/wrangler/src/__tests__/publish.test.ts
@@ -443,7 +443,7 @@ describe("publish", () => {
       expect(std.err).toMatchInlineSnapshot(`""`);
       expect(std.warn).toMatchInlineSnapshot(`
         "Processing wrangler.toml configuration:
-          - DEPRECATION: \\"build.upload.main\\":
+          - 🦺 DEPRECATION: \\"build.upload.main\\":
             Delete the \`build.upload.main\` and \`build.upload.dir\` fields.
             Then add the top level \`main\` field to your configuration file:
             \`\`\`
@@ -475,13 +475,13 @@ describe("publish", () => {
       expect(std.err).toMatchInlineSnapshot(`""`);
       expect(std.warn).toMatchInlineSnapshot(`
         "Processing ../wrangler.toml configuration:
-          - DEPRECATION: \\"build.upload.main\\":
+          - 🦺 DEPRECATION: \\"build.upload.main\\":
             Delete the \`build.upload.main\` and \`build.upload.dir\` fields.
             Then add the top level \`main\` field to your configuration file:
             \`\`\`
             main = \\"foo/index.js\\"
             \`\`\`
-          - DEPRECATION: \\"build.upload.dir\\":
+          - 🦺 DEPRECATION: \\"build.upload.dir\\":
             Use the top level \\"main\\" field or a command-line argument to specify the entry-point for the Worker."
       `);
     });
@@ -655,7 +655,7 @@ export default{
       await expect(runWrangler("publish ./index.js")).rejects
         .toThrowErrorMatchingInlineSnapshot(`
               "Processing wrangler.toml configuration:
-                - DEPRECATION: \\"site.entry-point\\":
+                - 🚨 NO LONGER SUPPORTED: \\"site.entry-point\\":
                   The \`site.entry-point\` config field is no longer used.
                   The entry-point should be specified via the command line or the \`main\` config field."
             `);
@@ -663,7 +663,7 @@ export default{
       expect(std.out).toMatchInlineSnapshot(`""`);
       expect(std.err).toMatchInlineSnapshot(`
         "Processing wrangler.toml configuration:
-          - DEPRECATION: \\"site.entry-point\\":
+          - 🚨 NO LONGER SUPPORTED: \\"site.entry-point\\":
             The \`site.entry-point\` config field is no longer used.
             The entry-point should be specified via the command line or the \`main\` config field.
 
diff --git a/packages/wrangler/src/__tests__/route.test.ts b/packages/wrangler/src/__tests__/route.test.ts
index 69c7d44231e1..92fe237d4845 100644
--- a/packages/wrangler/src/__tests__/route.test.ts
+++ b/packages/wrangler/src/__tests__/route.test.ts
@@ -9,7 +9,7 @@ describe("wrangler route", () => {
   it("shows a deprecation notice when `wrangler route` is run", async () => {
     await expect(runWrangler("route")).rejects
       .toThrowErrorMatchingInlineSnapshot(`
-            "DEPRECATION:
+            "🦺 DEPRECATION:
             \`wrangler route\` has been deprecated.
             Please use wrangler.toml and/or \`wrangler publish --routes\` to modify routes"
           `);
@@ -18,7 +18,7 @@ describe("wrangler route", () => {
   it("shows a deprecation notice when `wrangler route delete` is run", async () => {
     await expect(runWrangler("route delete")).rejects
       .toThrowErrorMatchingInlineSnapshot(`
-            "DEPRECATION:
+            "🦺 DEPRECATION:
             \`wrangler route delete\` has been deprecated.
             Remove the unwanted route(s) from wrangler.toml and run \`wrangler publish\` to remove your worker from those routes."
           `);
@@ -27,7 +27,7 @@ describe("wrangler route", () => {
   it("shows a deprecation notice when `wrangler route delete <id>` is run", async () => {
     await expect(runWrangler("route delete some-zone-id")).rejects
       .toThrowErrorMatchingInlineSnapshot(`
-            "DEPRECATION:
+            "🦺 DEPRECATION:
             \`wrangler route delete\` has been deprecated.
             Remove the unwanted route(s) from wrangler.toml and run \`wrangler publish\` to remove your worker from those routes."
           `);
@@ -36,7 +36,7 @@ describe("wrangler route", () => {
   it("shows a deprecation notice when `wrangler route list` is run", async () => {
     await expect(runWrangler("route list")).rejects
       .toThrowErrorMatchingInlineSnapshot(`
-            "DEPRECATION:
+            "🦺 DEPRECATION:
             \`wrangler route list\` has been deprecated.
             Refer to wrangler.toml for a list of routes the worker will be deployed to upon publishing.
             Refer to the Cloudflare Dashboard to see the routes this worker is currently running on."
diff --git a/packages/wrangler/src/config/validation-helpers.ts b/packages/wrangler/src/config/validation-helpers.ts
index 8b890a81c933..724b7625ecf4 100644
--- a/packages/wrangler/src/config/validation-helpers.ts
+++ b/packages/wrangler/src/config/validation-helpers.ts
@@ -16,10 +16,13 @@ export function deprecated<T extends object>(
   remove: boolean,
   breaking = false
 ): void {
+  const diagonsticMessage = breaking
+    ? `🚨 NO LONGER SUPPORTED: "${fieldPath}":\n${message}`
+    : `🦺 DEPRECATION: "${fieldPath}":\n${message}`;
   const result = unwindPropertyPath(config, fieldPath);
   if (result !== undefined && result.field in result.container) {
     (breaking ? diagnostics.errors : diagnostics.warnings).push(
-      `DEPRECATION: "${fieldPath}":\n${message}`
+      diagonsticMessage
     );
     if (remove) {
       delete (result.container as Record<string, unknown>)[result.field];
diff --git a/packages/wrangler/src/errors.ts b/packages/wrangler/src/errors.ts
index d183dfab2905..b3f96a1e8bde 100644
--- a/packages/wrangler/src/errors.ts
+++ b/packages/wrangler/src/errors.ts
@@ -1,6 +1,6 @@
 export class DeprecationError extends Error {
   constructor(message: string) {
-    super(`DEPRECATION:\n${message}`);
+    super(`🦺 DEPRECATION:\n${message}`);
   }
 }