diff --git a/src/actions/baseMotion.ts b/src/actions/baseMotion.ts
index aa658f11f7f..d025ff3dd84 100644
--- a/src/actions/baseMotion.ts
+++ b/src/actions/baseMotion.ts
@@ -119,6 +119,10 @@ export abstract class BaseMovement extends BaseAction {
       result = await this.createMovementResult(position, vimState, recordedState, lastIteration);
 
       if (result instanceof Position) {
+        /**
+         * This position will be passed to the `motion` on the next iteration,
+         * it may cause some issues when count > 1.
+         */
         position = result;
       } else if (isIMovement(result)) {
         if (prevResult && result.failed) {
diff --git a/src/actions/motion.ts b/src/actions/motion.ts
index 16f5cf393e6..5474b497cd6 100644
--- a/src/actions/motion.ts
+++ b/src/actions/motion.ts
@@ -1,6 +1,6 @@
 import * as vscode from 'vscode';
 
-import { ChangeOperator, DeleteOperator, YankOperator } from './operator';
+import { ChangeOperator, DeleteOperator, YankOperator, BaseOperator } from './operator';
 import { CursorMoveByUnit, CursorMovePosition, TextEditor } from './../textEditor';
 import { Mode } from './../mode/mode';
 import { PairMatcher } from './../common/matching/matcher';
@@ -1257,17 +1257,54 @@ class MoveNextSentenceBegin extends BaseMovement {
 class MoveParagraphEnd extends BaseMovement {
   keys = ['}'];
   isJump = true;
+  iteration = 0;
+  isFirstLineWise = false;
 
   public async execAction(position: Position, vimState: VimState): Promise<Position> {
-    const isLineWise =
-      position.isLineBeginning() &&
-      vimState.currentMode === Mode.Normal &&
-      vimState.recordedState.operator;
-    let paragraphEnd = position.getCurrentParagraphEnd();
-    vimState.currentRegisterMode = isLineWise
-      ? RegisterMode.LineWise
-      : RegisterMode.AscertainFromCurrentMode;
-    return isLineWise ? paragraphEnd.getLeftThroughLineBreaks(true) : paragraphEnd;
+    const hasOperator = vimState.recordedState.operator;
+    const paragraphEnd = position.getCurrentParagraphEnd();
+
+    if (hasOperator) {
+      /**
+       * When paired with an `operator` and a `count` this move will be executed
+       * multiple times which could cause issues like https://github.com/VSCodeVim/Vim/issues/4488
+       * because subsequent runs will receive back whatever position we return
+       * (See comment in `BaseMotion.execActionWithCount()`).
+       *
+       * We keep track of the iteration we are in, this way we can
+       * return the correct position when on the last iteration, and we don't
+       * accidentally set the `registerMode` incorrectly.
+       */
+      this.iteration++;
+
+      const isLineWise = position.isLineBeginning() && vimState.currentMode === Mode.Normal;
+
+      const isLastIteration = vimState.recordedState.count
+        ? vimState.recordedState.count === this.iteration
+        : true;
+
+      /**
+       * `position` may not represent the position of the cursor from which the command was initiated.
+       * In the case that we will be repeating this move more than once
+       * we want to respect whether the starting position was at the beginning of line or not.
+       */
+      this.isFirstLineWise = this.iteration === 1 ? isLineWise : this.isFirstLineWise;
+
+      vimState.currentRegisterMode = this.isFirstLineWise
+        ? RegisterMode.LineWise
+        : RegisterMode.AscertainFromCurrentMode;
+
+      /**
+       * `paragraphEnd` is the first blank line after the last word in the
+       * current paragraph, we want the position just before that one to
+       * accurately emulate Vim's behaviour, unless we are at EOF.
+       */
+      return isLastIteration && !paragraphEnd.isAtDocumentEnd()
+        ? paragraphEnd.getLeftThroughLineBreaks(true)
+        : paragraphEnd;
+    }
+
+    return paragraphEnd;
   }
 }
 
diff --git a/test/mode/modeNormal.test.ts b/test/mode/modeNormal.test.ts
index 603f2093c40..9749bfb459f 100644
--- a/test/mode/modeNormal.test.ts
+++ b/test/mode/modeNormal.test.ts
@@ -1003,7 +1003,7 @@ suite('Mode Normal', () => {
   });
 
   newTest({
-    title: 'Can handle d}',
+    title: 'Can handle d} at beginning of line',
     start: ['|foo', 'bar', '', 'fun'],
     keysPressed: 'd}',
     end: ['|', 'fun'],
@@ -1018,6 +1018,30 @@ suite('Mode Normal', () => {
     endMode: Mode.Normal,
   });
 
+  newTest({
+    title: 'Can handle d} when not at beginning of line',
+    start: ['f|oo', 'bar', '', 'fun'],
+    keysPressed: 'd}',
+    end: ['|f', '', 'fun'],
+    endMode: Mode.Normal,
+  });
+
+  newTest({
+    title: 'Can handle } with operator and count, at beginning of line',
+    start: ['|foo', '', 'bar', '', 'fun'],
+    keysPressed: 'd2}',
+    end: ['|', 'fun'],
+    endMode: Mode.Normal,
+  });
+
+  newTest({
+    title: 'Can handle } with operator and count, and not at beginning of line',
+    start: ['f|oo', '', 'bar', '', 'fun'],
+    keysPressed: 'd2}',
+    end: ['|f', '', 'fun'],
+    endMode: Mode.Normal,
+  });
+
   newTest({
     title: 'Select sentence with trailing spaces',
     start: ["That's my sec|ret, Captain. I'm always angry."],