diff --git a/.chronus/changes/fix-deprecated-operation-import-2026-6-5-18-8-6.md b/.chronus/changes/fix-deprecated-operation-import-2026-6-5-18-8-6.md
new file mode 100644
index 00000000000..c7c3a8d8f2e
--- /dev/null
+++ b/.chronus/changes/fix-deprecated-operation-import-2026-6-5-18-8-6.md
@@ -0,0 +1,7 @@
+---
+changeKind: fix
+packages:
+  - "@typespec/openapi3"
+---
+
+Fix import of `deprecated: true` on OpenAPI3 operations to generate `#deprecated "deprecated"` directive in converted TypeSpec output.
diff --git a/packages/openapi3/src/cli/actions/convert/generators/generate-operation.ts b/packages/openapi3/src/cli/actions/convert/generators/generate-operation.ts
index fa704c611f3..1eaf24e3441 100644
--- a/packages/openapi3/src/cli/actions/convert/generators/generate-operation.ts
+++ b/packages/openapi3/src/cli/actions/convert/generators/generate-operation.ts
@@ -6,19 +6,23 @@ import {
 } from "../interfaces.js";
 import { Context } from "../utils/context.js";
 import { generateDocs } from "../utils/docs.js";
-import { generateDecorators } from "./generate-decorators.js";
+import { generateDecorators, generateDirectives } from "./generate-decorators.js";
 import { generateOperationReturnType } from "./generate-response-expressions.js";
 
 export function generateOperation(operation: TypeSpecOperation, context: Context): string {
-  const definitions: string[] = [];
+  const preamble: string[] = [];
+  const operationParts: string[] = [];
 
   if (operation.doc) {
-    definitions.push(generateDocs(operation.doc));
+    preamble.push(generateDocs(operation.doc));
   }
 
-  definitions.push(...operation.tags.map((t) => `@tag("${t}")`));
+  // Directives (e.g. #deprecated) must each be on their own line before the operation
+  preamble.push(...generateDirectives(operation.directives));
+
+  operationParts.push(...operation.tags.map((t) => `@tag("${t}")`));
 
-  definitions.push(generateDecorators(operation.decorators).join(" "));
+  operationParts.push(generateDecorators(operation.decorators).join(" "));
 
   // generate parameters
   const parameters: string[] = [
@@ -29,12 +33,15 @@ export function generateOperation(operation: TypeSpecOperation, context: Context
   const responses = generateOperationReturnType(operation, context);
 
   if (operation.fixmes?.length) {
-    definitions.push("\n", ...operation.fixmes.map((f) => `// FIXME: ${f}\n`));
+    operationParts.push("\n", ...operation.fixmes.map((f) => `// FIXME: ${f}\n`));
   }
 
-  definitions.push(`op ${operation.name}(${parameters.join(", ")}): ${responses};`);
+  operationParts.push(`op ${operation.name}(${parameters.join(", ")}): ${responses};`);
 
-  return definitions.join(" ");
+  const preambleStr = preamble.join("\n");
+  const operationStr = operationParts.join(" ");
+
+  return preambleStr ? `${preambleStr}\n${operationStr}` : operationStr;
 }
 
 function generateOperationParameter(
diff --git a/packages/openapi3/src/cli/actions/convert/transforms/transform-paths.ts b/packages/openapi3/src/cli/actions/convert/transforms/transform-paths.ts
index 21fd50ff38d..30e2d0ae0a8 100644
--- a/packages/openapi3/src/cli/actions/convert/transforms/transform-paths.ts
+++ b/packages/openapi3/src/cli/actions/convert/transforms/transform-paths.ts
@@ -9,6 +9,7 @@ import {
   Refable,
 } from "../../../../types.js";
 import {
+  TypeSpecDirective,
   TypeSpecOperation,
   TypeSpecOperationParameter,
   TypeSpecRequestBody,
@@ -75,6 +76,10 @@ export function transformPaths(
 
       const requestBodies = transformRequestBodies(operation.requestBody, context);
 
+      const directives: TypeSpecDirective[] = operation.deprecated
+        ? [{ name: "deprecated", message: "deprecated" }]
+        : [];
+
       // Check if we need to split the operation due to incompatible content types
       const splitOperations = splitOperationByContentType(
         operationId,
@@ -85,6 +90,7 @@ export function transformPaths(
         operationResponses,
         tags,
         fixmes,
+        directives,
         usedOperationIds,
       );
 
@@ -161,6 +167,7 @@ function splitOperationByContentType(
   responses: any,
   tags: string[],
   fixmes: string[],
+  directives: TypeSpecDirective[],
   usedOperationIds: Set<string>,
 ): TypeSpecOperation[] {
   // If no request bodies or only one content type, no splitting needed
@@ -169,6 +176,7 @@ function splitOperationByContentType(
       {
         ...getScopeAndName(operationId),
         decorators,
+        directives,
         parameters,
         doc,
         operationId,
@@ -190,6 +198,7 @@ function splitOperationByContentType(
       {
         ...getScopeAndName(operationId),
         decorators,
+        directives,
         parameters,
         doc,
         operationId,
@@ -248,6 +257,7 @@ function splitOperationByContentType(
     operations.push({
       ...getScopeAndName(newOperationId),
       decorators: newDecorators,
+      directives,
       parameters,
       doc,
       operationId: newOperationId,
diff --git a/packages/openapi3/test/tsp-openapi3/convert-openapi3-doc.test.ts b/packages/openapi3/test/tsp-openapi3/convert-openapi3-doc.test.ts
index 8a7289f0ccf..61c6ca3fdfe 100644
--- a/packages/openapi3/test/tsp-openapi3/convert-openapi3-doc.test.ts
+++ b/packages/openapi3/test/tsp-openapi3/convert-openapi3-doc.test.ts
@@ -941,6 +941,116 @@ def grade(sample: dict, item: dict) -> float:
       ),
     );
   });
+
+  it("should convert deprecated operation without description to #deprecated directive", async () => {
+    const tsp = await convertOpenAPI3Document({
+      openapi: version,
+      info: {
+        title: "(title)",
+        version: "0.0.0",
+      },
+      tags: [],
+      paths: {
+        "/foo": {
+          get: {
+            operationId: "Foo_get",
+            deprecated: true,
+            tags: ["Foo"],
+            responses: {
+              "200": {
+                description: "OK",
+              },
+            },
+          },
+        },
+      },
+    } as any);
+
+    strictEqual(
+      tsp,
+      await formatTypeSpec(
+        `
+        import "@typespec/http";
+        import "@typespec/openapi";
+        import "@typespec/openapi3";
+
+        using Http;
+        using OpenAPI;
+
+        @service(#{
+          title: "(title)",
+        })
+        @info(#{
+          version: "0.0.0",
+        })
+        namespace title;
+
+        #deprecated "deprecated"
+        @tag("Foo")
+        @route("/foo")
+        @get
+        op Foo_get(): OkResponse;
+        `,
+        { printWidth: 100, tabWidth: 2 },
+      ),
+    );
+  });
+
+  it("should convert deprecated operation with description to #deprecated directive", async () => {
+    const tsp = await convertOpenAPI3Document({
+      openapi: version,
+      info: {
+        title: "(title)",
+        version: "0.0.0",
+      },
+      tags: [],
+      paths: {
+        "/foo": {
+          get: {
+            operationId: "Foo_get",
+            description: "Get foo",
+            deprecated: true,
+            tags: ["Foo"],
+            responses: {
+              "200": {
+                description: "OK",
+              },
+            },
+          },
+        },
+      },
+    } as any);
+
+    strictEqual(
+      tsp,
+      await formatTypeSpec(
+        `
+        import "@typespec/http";
+        import "@typespec/openapi";
+        import "@typespec/openapi3";
+
+        using Http;
+        using OpenAPI;
+
+        @service(#{
+          title: "(title)",
+        })
+        @info(#{
+          version: "0.0.0",
+        })
+        namespace title;
+
+        /** Get foo */
+        #deprecated "deprecated"
+        @tag("Foo")
+        @route("/foo")
+        @get
+        op Foo_get(): OkResponse;
+        `,
+        { printWidth: 100, tabWidth: 2 },
+      ),
+    );
+  });
 });
 
 describe("convertOpenAPI3Document tag metadata", () => {