diff --git a/lib/modules/versioning/pep440/index.spec.ts b/lib/modules/versioning/pep440/index.spec.ts
index 84fe37c5090bd9..09db07eef1d56f 100644
--- a/lib/modules/versioning/pep440/index.spec.ts
+++ b/lib/modules/versioning/pep440/index.spec.ts
@@ -192,6 +192,123 @@ describe('modules/versioning/pep440/index', () => {
     }
   );
 
+  test.each`
+    currentValue            | rangeStrategy    | currentVersion | newVersion   | expected
+    ${'1.0.0'}              | ${'bump'}        | ${'1.0.0'}     | ${'1.2.3'}   | ${'1.2.3'}
+    ${'1.0.0'}              | ${'replace'}     | ${'1.0.0'}     | ${'1.2.3'}   | ${'1.2.3'}
+    ${'1.0.0'}              | ${'pin'}         | ${'1.0.0'}     | ${'1.2.3'}   | ${'1.2.3'}
+    ${'==1.0.3'}            | ${'bump'}        | ${'1.0.0'}     | ${'1.2.3'}   | ${'1.2.3'}
+    ${'==1.0.3'}            | ${'replace'}     | ${'1.0.0'}     | ${'1.2.3'}   | ${'1.2.3'}
+    ${'==1.0.3'}            | ${'pin'}         | ${'1.0.0'}     | ${'1.2.3'}   | ${'1.2.3'}
+    ${'>=1.2.0'}            | ${'bump'}        | ${'1.0.0'}     | ${'1.2.3'}   | ${'1.2.3'}
+    ${'>=1.2.0'}            | ${'replace'}     | ${'1.0.0'}     | ${'1.2.3'}   | ${'1.2.3'}
+    ${'~=1.2.0'}            | ${'bump'}        | ${'1.0.0'}     | ${'1.2.3'}   | ${'1.2.3'}
+    ${'~=1.2.0'}            | ${'replace'}     | ${'1.0.0'}     | ${'1.2.3'}   | ${'1.2.3'}
+    ${'>=1.2.0'}            | ${'pin'}         | ${'1.0.0'}     | ${'1.2.3'}   | ${'1.2.3'}
+    ${'~=1.2.0'}            | ${'pin'}         | ${'1.0.0'}     | ${'1.2.3'}   | ${'1.2.3'}
+    ${'~=1.0.3'}            | ${'bump'}        | ${'1.0.0'}     | ${'1.2.3'}   | ${'1.2.3'}
+    ${'~=1.0.3'}            | ${'replace'}     | ${'1.0.0'}     | ${'1.2.3'}   | ${'1.2.3'}
+    ${'~=1.0.3'}            | ${'pin'}         | ${'1.0.0'}     | ${'1.2.3'}   | ${'1.2.3'}
+    ${'==1.2.*'}            | ${'bump'}        | ${'1.0.0'}     | ${'1.2.3'}   | ${'1.2.3'}
+    ${'==1.2.*'}            | ${'replace'}     | ${'1.0.0'}     | ${'1.2.3'}   | ${'1.2.3'}
+    ${'==1.2.*'}            | ${'pin'}         | ${'1.0.0'}     | ${'1.2.3'}   | ${'1.2.3'}
+    ${'==1.0.*'}            | ${'bump'}        | ${'1.0.0'}     | ${'1.2.3'}   | ${'1.2.3'}
+    ${'==1.0.*'}            | ${'replace'}     | ${'1.0.0'}     | ${'1.2.3'}   | ${'1.2.3'}
+    ${'==1.0.*'}            | ${'pin'}         | ${'1.0.0'}     | ${'1.2.3'}   | ${'1.2.3'}
+    ${'<1.2.2.3'}           | ${'bump'}        | ${'1.0.0'}     | ${'1.2.3'}   | ${'1.2.3'}
+    ${'<1.2.2.3'}           | ${'pin'}         | ${'1.0.0'}     | ${'1.2.3'}   | ${'1.2.3'}
+    ${'<1.2.3'}             | ${'bump'}        | ${'1.0.0'}     | ${'1.2.3'}   | ${'1.2.3'}
+    ${'<1.2.3'}             | ${'replace'}     | ${'1.0.0'}     | ${'1.2.3'}   | ${'1.2.3'}
+    ${'<1.2.3'}             | ${'pin'}         | ${'1.0.0'}     | ${'1.2.3'}   | ${'1.2.3'}
+    ${'<1.2'}               | ${'bump'}        | ${'1.0.0'}     | ${'1.2.3'}   | ${'1.2.3'}
+    ${'<1.2'}               | ${'replace'}     | ${'1.0.0'}     | ${'1.2.3'}   | ${'1.2.3'}
+    ${'<1.2'}               | ${'pin'}         | ${'1.0.0'}     | ${'1.2.3'}   | ${'1.2.3'}
+    ${'<1'}                 | ${'bump'}        | ${'1.0.0'}     | ${'1.2.3'}   | ${'1.2.3'}
+    ${'<1'}                 | ${'replace'}     | ${'1.0.0'}     | ${'1.2.3'}   | ${'1.2.3'}
+    ${'<1'}                 | ${'pin'}         | ${'1.0.0'}     | ${'1.2.3'}   | ${'1.2.3'}
+    ${'<2.0.0'}             | ${'bump'}        | ${'1.0.0'}     | ${'1.2.3'}   | ${'1.2.3'}
+    ${'<2.0.0'}             | ${'replace'}     | ${'1.0.0'}     | ${'1.2.3'}   | ${'1.2.3'}
+    ${'<2.0.0'}             | ${'pin'}         | ${'1.0.0'}     | ${'1.2.3'}   | ${'1.2.3'}
+    ${'>0.9.8'}             | ${'bump'}        | ${'1.0.0'}     | ${'1.2.3'}   | ${'1.2.3'}
+    ${'>0.9.8'}             | ${'replace'}     | ${'1.0.0'}     | ${'1.2.3'}   | ${'1.2.3'}
+    ${'>0.9.8'}             | ${'pin'}         | ${'1.0.0'}     | ${'1.2.3'}   | ${'1.2.3'}
+    ${'>2.0.0'}             | ${'bump'}        | ${'1.0.0'}     | ${'1.2.3'}   | ${'1.2.3'}
+    ${'>2.0.0'}             | ${'replace'}     | ${'1.0.0'}     | ${'1.2.3'}   | ${'1.2.3'}
+    ${'>2.0.0'}             | ${'pin'}         | ${'1.0.0'}     | ${'1.2.3'}   | ${'1.2.3'}
+    ${'>=2.0.0'}            | ${'bump'}        | ${'1.0.0'}     | ${'1.2.3'}   | ${'1.2.3'}
+    ${'>=2.0.0'}            | ${'replace'}     | ${'1.0.0'}     | ${'1.2.3'}   | ${'1.2.3'}
+    ${'>=2.0.0'}            | ${'pin'}         | ${'1.0.0'}     | ${'1.2.3'}   | ${'1.2.3'}
+    ${'~=1.1.0, !=1.1.1'}   | ${'bump'}        | ${'1.0.0'}     | ${'1.2.3'}   | ${'1.2.3'}
+    ${'~=1.1.0, !=1.1.1'}   | ${'replace'}     | ${'1.0.0'}     | ${'1.2.3'}   | ${'1.2.3'}
+    ${'~=1.1.0, !=1.1.1'}   | ${'pin'}         | ${'1.0.0'}     | ${'1.2.3'}   | ${'1.2.3'}
+    ${'~=1.1.0,!=1.1.1'}    | ${'bump'}        | ${'1.0.0'}     | ${'1.2.3'}   | ${'1.2.3'}
+    ${'~=1.1.0,!=1.1.1'}    | ${'replace'}     | ${'1.0.0'}     | ${'1.2.3'}   | ${'1.2.3'}
+    ${'~=1.1.0,!=1.1.1'}    | ${'pin'}         | ${'1.0.0'}     | ${'1.2.3'}   | ${'1.2.3'}
+    ${' '}                  | ${'bump'}        | ${'1.0.0'}     | ${'1.2.3'}   | ${'1.2.3'}
+    ${' '}                  | ${'replace'}     | ${'1.0.0'}     | ${'1.2.3'}   | ${'1.2.3'}
+    ${' '}                  | ${'pin'}         | ${'1.0.0'}     | ${'1.2.3'}   | ${'1.2.3'}
+    ${'invalid'}            | ${'bump'}        | ${'1.0.0'}     | ${'1.2.3'}   | ${'1.2.3'}
+    ${'invalid'}            | ${'replace'}     | ${'1.0.0'}     | ${'1.2.3'}   | ${'1.2.3'}
+    ${'invalid'}            | ${'pin'}         | ${'1.0.0'}     | ${'1.2.3'}   | ${'1.2.3'}
+    ${'===1.0.3'}           | ${'bump'}        | ${'1.0.0'}     | ${'1.2.3'}   | ${'1.2.3'}
+    ${'===1.0.3'}           | ${'replace'}     | ${'1.0.0'}     | ${'1.2.3'}   | ${'1.2.3'}
+    ${'===1.0.3'}           | ${'pin'}         | ${'1.0.0'}     | ${'1.2.3'}   | ${'1.2.3'}
+    ${'!=1.2.3'}            | ${'bump'}        | ${'1.0.0'}     | ${'1.2.3'}   | ${'1.2.3'}
+    ${'!=1.2.3'}            | ${'replace'}     | ${'1.0.0'}     | ${'1.2.3'}   | ${'1.2.3'}
+    ${'!=1.2.3'}            | ${'pin'}         | ${'1.0.0'}     | ${'1.2.3'}   | ${'1.2.3'}
+    ${'~=1.1.0,!=1.1.1'}    | ${'unsupported'} | ${'1.0.0'}     | ${'1.2.3'}   | ${'1.2.3'}
+    ${'>=19.12.2,<20.13.9'} | ${'replace'}     | ${'19.12.2'}   | ${'21.3.1'}  | ${'21.3.1'}
+    ${'>=19.12.2,<19.13.9'} | ${'replace'}     | ${'19.12.2'}   | ${'20.3.1'}  | ${'20.3.1'}
+    ${'>=19.12.2,<19.13.0'} | ${'replace'}     | ${'19.12.2'}   | ${'20.3.1'}  | ${'20.3.1'}
+    ${'>=19.12.2,<19.13.0'} | ${'replace'}     | ${'19.12.2'}   | ${'20.3.0'}  | ${'20.3.0'}
+    ${'>=19.12.2,<19.13.0'} | ${'replace'}     | ${'19.12.2'}   | ${'19.13.1'} | ${'19.13.1'}
+    ${'>=19.12.2,<19.13.0'} | ${'replace'}     | ${'19.12.2'}   | ${'19.13.0'} | ${'19.13.0'}
+    ${'>=19.12.2,<19.13.0'} | ${'auto'}        | ${'19.12.2'}   | ${'19.13.0'} | ${'19.13.0'}
+    ${'>=19.12.2,<20.13.9'} | ${'widen'}       | ${'19.12.2'}   | ${'21.3.1'}  | ${'21.3.1'}
+    ${'>=19.12.2,<19.13.9'} | ${'widen'}       | ${'19.12.2'}   | ${'20.3.1'}  | ${'20.3.1'}
+    ${'>=19.12.2,<19.13.0'} | ${'widen'}       | ${'19.12.2'}   | ${'20.3.1'}  | ${'20.3.1'}
+    ${'>=19.12.2,<19.13.0'} | ${'widen'}       | ${'19.12.2'}   | ${'20.3.0'}  | ${'20.3.0'}
+    ${'>=19.12.2,<19.13.0'} | ${'widen'}       | ${'19.12.2'}   | ${'19.13.1'} | ${'19.13.1'}
+    ${'>=19.12.2,<19.13.0'} | ${'widen'}       | ${'19.12.2'}   | ${'19.13.0'} | ${'19.13.0'}
+    ${'~=7.2'}              | ${'replace'}     | ${'7.2.0'}     | ${'8.0.1'}   | ${'8.0.1'}
+    ${'~=7.2'}              | ${'replace'}     | ${'7.2.0'}     | ${'8'}       | ${'8'}
+    ${'~=7.2.0'}            | ${'replace'}     | ${'7.2.0'}     | ${'8.2'}     | ${'8.2'}
+    ${'~=7.2'}              | ${'widen'}       | ${'7.2.0'}     | ${'8.0.1'}   | ${'8.0.1'}
+    ${'~=7.2'}              | ${'widen'}       | ${'7.2.0'}     | ${'8'}       | ${'8'}
+    ${'~=7.2.0'}            | ${'widen'}       | ${'7.2.0'}     | ${'8.2'}     | ${'8.2'}
+    ${'==3.2.*,>=3.2.2'}    | ${'replace'}     | ${'3.2.2'}     | ${'4.1.1'}   | ${'4.1.1'}
+    ${'==3.2.*,>=3.2.2'}    | ${'replace'}     | ${'3.2.2'}     | ${'4.0.0'}   | ${'4.0.0'}
+    ${'>=1.0.0,<1.1.0'}     | ${'replace'}     | ${'1.0.0'}     | ${'1.2.0'}   | ${'1.2.0'}
+    ${'<1.3.0'}             | ${'bump'}        | ${'1.3.0'}     | ${'0.9.2'}   | ${'0.9.2'}
+    ${'<1.3.0'}             | ${'bump'}        | ${'0.9.0'}     | ${'0.9.2'}   | ${'0.9.2'}
+    ${'<=1.3.0'}            | ${'bump'}        | ${'0.9.0'}     | ${'0.9.2'}   | ${'0.9.2'}
+    ${'<=1.3.0'}            | ${'bump'}        | ${'1.3.0'}     | ${'0.9.2'}   | ${'0.9.2'}
+    ${'<1.3.0'}             | ${'bump'}        | ${'1.3.0'}     | ${'1.6.0'}   | ${'1.6.0'}
+    ${'<1.3.0'}             | ${'bump'}        | ${'0.9.0'}     | ${'1.6.0'}   | ${'1.6.0'}
+    ${'<=1.3.0'}            | ${'bump'}        | ${'0.9.0'}     | ${'1.6.0'}   | ${'1.6.0'}
+    ${'<=1.3.0'}            | ${'bump'}        | ${'1.3.0'}     | ${'1.6.0'}   | ${'1.6.0'}
+    ${'1.0.0'}              | ${'bump'}        | ${'1.0.0'}     | ${'==1.2.3'} | ${'==1.2.3'}
+    ${'1.0.0'}              | ${'bump'}        | ${'1.0.0'}     | ${'>=1.2.3'} | ${'>=1.2.3'}
+    ${'1.0.0'}              | ${'bump'}        | ${'1.0.0'}     | ${'<=1.2.3'} | ${'<=1.2.3'}
+    ${'1.0.0'}              | ${'bump'}        | ${'1.0.0'}     | ${'~=1.2.3'} | ${'~=1.2.3'}
+    ${'1.0.0'}              | ${'bump'}        | ${'1.0.0'}     | ${'!=1.2.3'} | ${'!=1.2.3'}
+    ${'1.0.0'}              | ${'bump'}        | ${'1.0.0'}     | ${'>1.2.3'}  | ${'>1.2.3'}
+    ${'1.0.0'}              | ${'bump'}        | ${'1.0.0'}     | ${'<1.2.3'}  | ${'<1.2.3'}
+  `(
+    'getNewValue("$currentValue", "$rangeStrategy", "$currentVersion", "$newVersion") === "$expected"',
+    ({ currentValue, rangeStrategy, currentVersion, newVersion, expected }) => {
+      const isReplacement = true;
+      const res = pep440.getNewValue({
+        currentValue,
+        rangeStrategy,
+        currentVersion,
+        newVersion,
+        isReplacement,
+      });
+      expect(res).toEqual(expected);
+    }
+  );
+
   test.each`
     version      | range                  | expected
     ${'0.9.9.9'} | ${'>= 1.0.0, < 2.0.0'} | ${true}
diff --git a/lib/modules/versioning/pep440/range.ts b/lib/modules/versioning/pep440/range.ts
index ab112037079b31..5e2dde8ef8bf16 100644
--- a/lib/modules/versioning/pep440/range.ts
+++ b/lib/modules/versioning/pep440/range.ts
@@ -94,15 +94,16 @@ export function getNewValue({
   rangeStrategy,
   currentVersion,
   newVersion,
+  isReplacement,
 }: NewValueConfig): string | null {
   let ranges: Range[];
   let updatedRange: (string | null)[];
-  if (rangeStrategy === 'pin') {
+  if (rangeStrategy === 'pin' && !isReplacement) {
     return '==' + newVersion;
   }
 
   // no symbol: accept only that specific version specified
-  if (currentValue === currentVersion) {
+  if (currentValue === currentVersion || isReplacement) {
     return newVersion;
   }
 
diff --git a/lib/modules/versioning/types.ts b/lib/modules/versioning/types.ts
index 838431e809f005..608d08e71031e7 100644
--- a/lib/modules/versioning/types.ts
+++ b/lib/modules/versioning/types.ts
@@ -6,6 +6,7 @@ export interface NewValueConfig {
   rangeStrategy: RangeStrategy;
   currentVersion?: string;
   newVersion: string;
+  isReplacement?: boolean;
 }
 export interface VersioningApi {
   // validation
diff --git a/lib/workers/repository/process/lookup/index.ts b/lib/workers/repository/process/lookup/index.ts
index 19b076d7dd7dc5..816381d7a42bca 100644
--- a/lib/workers/repository/process/lookup/index.ts
+++ b/lib/workers/repository/process/lookup/index.ts
@@ -163,6 +163,7 @@ export async function lookupUpdates(
             currentValue: currentValue!,
             newVersion: config.replacementVersion,
             rangeStrategy: rangeStrategy!,
+            isReplacement: true,
           })!,
         });
       }