diff --git a/packages/ngtools/webpack/src/paths-plugin.ts b/packages/ngtools/webpack/src/paths-plugin.ts
index e9aab5831f24..60f845ccd140 100644
--- a/packages/ngtools/webpack/src/paths-plugin.ts
+++ b/packages/ngtools/webpack/src/paths-plugin.ts
@@ -7,7 +7,7 @@
  */
 
 import * as path from 'path';
-import { CompilerOptions, MapLike } from 'typescript';
+import { CompilerOptions } from 'typescript';
 import type { Configuration } from 'webpack';
 
 // eslint-disable-next-line @typescript-eslint/no-empty-interface
@@ -16,21 +16,98 @@ export interface TypeScriptPathsPluginOptions extends Pick<CompilerOptions, 'pat
 // Extract Resolver type from Webpack types since it is not directly exported
 type Resolver = Exclude<Exclude<Configuration['resolve'], undefined>['resolver'], undefined>;
 
+interface PathPattern {
+  starIndex: number;
+  prefix: string;
+  suffix?: string;
+  potentials: { hasStar: boolean; prefix: string; suffix?: string }[];
+}
+
 export class TypeScriptPathsPlugin {
-  constructor(private options?: TypeScriptPathsPluginOptions) {}
+  private baseUrl?: string;
+  private patterns?: PathPattern[];
+
+  constructor(options?: TypeScriptPathsPluginOptions) {
+    if (options) {
+      this.update(options);
+    }
+  }
 
+  /**
+   * Update the plugin with new path mapping option values.
+   * The options will also be preprocessed to reduce the overhead of individual resolve actions
+   * during a build.
+   *
+   * @param options The `paths` and `baseUrl` options from TypeScript's `CompilerOptions`.
+   */
   update(options: TypeScriptPathsPluginOptions): void {
-    this.options = options;
+    this.baseUrl = options.baseUrl;
+    this.patterns = undefined;
+
+    if (options.paths) {
+      for (const [pattern, potentials] of Object.entries(options.paths)) {
+        // Ignore any entries that would not result in a new mapping
+        if (potentials.length === 0 || potentials.every((potential) => potential === '*')) {
+          continue;
+        }
+
+        const starIndex = pattern.indexOf('*');
+        let prefix = pattern;
+        let suffix;
+        if (starIndex > -1) {
+          prefix = pattern.slice(0, starIndex);
+          if (starIndex < pattern.length - 1) {
+            suffix = pattern.slice(starIndex + 1);
+          }
+        }
+
+        this.patterns ??= [];
+        this.patterns.push({
+          starIndex,
+          prefix,
+          suffix,
+          potentials: potentials.map((potential) => {
+            const potentialStarIndex = potential.indexOf('*');
+            if (potentialStarIndex === -1) {
+              return { hasStar: false, prefix: potential };
+            }
+
+            return {
+              hasStar: true,
+              prefix: potential.slice(0, potentialStarIndex),
+              suffix:
+                potentialStarIndex < potential.length - 1
+                  ? potential.slice(potentialStarIndex + 1)
+                  : undefined,
+            };
+          }),
+        });
+      }
+
+      // Sort patterns so that exact matches take priority then largest prefix match
+      this.patterns?.sort((a, b) => {
+        if (a.starIndex === -1) {
+          return -1;
+        } else if (b.starIndex === -1) {
+          return 1;
+        } else {
+          return b.starIndex - a.starIndex;
+        }
+      });
+    }
   }
 
   apply(resolver: Resolver): void {
     const target = resolver.ensureHook('resolve');
 
+    // To support synchronous resolvers this hook cannot be promise based.
+    // Webpack supports synchronous resolution with `tap` and `tapAsync` hooks.
     resolver.getHook('described-resolve').tapAsync(
       'TypeScriptPathsPlugin',
       // eslint-disable-next-line @typescript-eslint/no-explicit-any
       (request: any, resolveContext, callback) => {
-        if (!this.options) {
+        // Preprocessing of the options will ensure that `patterns` is either undefined or has elements to check
+        if (!this.patterns) {
           callback();
 
           return;
@@ -50,31 +127,37 @@ export class TypeScriptPathsPlugin {
         }
 
         // Only work on Javascript/TypeScript issuers.
-        if (!request.context.issuer || !request.context.issuer.match(/\.[jt]sx?$/)) {
+        if (!request.context.issuer || !request.context.issuer.match(/\.[cm]?[jt]sx?$/)) {
           callback();
 
           return;
         }
 
-        // Relative or absolute requests are not mapped
-        if (originalRequest.startsWith('.') || originalRequest.startsWith('/')) {
-          callback();
-
-          return;
-        }
-
-        // Ignore all webpack special requests
-        if (originalRequest.startsWith('!!')) {
-          callback();
+        switch (originalRequest[0]) {
+          case '.':
+          case '/':
+            // Relative or absolute requests are not mapped
+            callback();
 
-          return;
+            return;
+          case '!':
+            // Ignore all webpack special requests
+            if (originalRequest.length > 1 && originalRequest[1] === '!') {
+              callback();
+
+              return;
+            }
+            break;
         }
 
-        const replacements = findReplacements(originalRequest, this.options.paths || {});
+        // A generator is used to limit the amount of replacements that need to be created.
+        // For example, if the first one resolves, any others are not needed and do not need
+        // to be created.
+        const replacements = findReplacements(originalRequest, this.patterns);
 
         const tryResolve = () => {
-          const potential = replacements.shift();
-          if (!potential) {
+          const next = replacements.next();
+          if (next.done) {
             callback();
 
             return;
@@ -82,7 +165,7 @@ export class TypeScriptPathsPlugin {
 
           const potentialRequest = {
             ...request,
-            request: path.resolve(this.options?.baseUrl || '', potential),
+            request: path.resolve(this.baseUrl ?? '', next.value),
             typescriptPathMapped: true,
           };
 
@@ -110,89 +193,52 @@ export class TypeScriptPathsPlugin {
   }
 }
 
-function findReplacements(originalRequest: string, paths: MapLike<string[]>): string[] {
+function* findReplacements(
+  originalRequest: string,
+  patterns: PathPattern[],
+): IterableIterator<string> {
   // check if any path mapping rules are relevant
-  const pathMapOptions = [];
-  for (const pattern in paths) {
-    // get potentials and remove duplicates; JS Set maintains insertion order
-    const potentials = Array.from(new Set(paths[pattern]));
-    if (potentials.length === 0) {
-      // no potential replacements so skip
-      continue;
-    }
+  for (const { starIndex, prefix, suffix, potentials } of patterns) {
+    let partial;
 
-    // can only contain zero or one
-    const starIndex = pattern.indexOf('*');
     if (starIndex === -1) {
-      if (pattern === originalRequest) {
-        pathMapOptions.push({
-          starIndex,
-          partial: '',
-          potentials,
-        });
-      }
-    } else if (starIndex === 0 && pattern.length === 1) {
-      if (potentials.length === 1 && potentials[0] === '*') {
-        // identity mapping -> noop
-        continue;
+      // No star means an exact match is required
+      if (prefix === originalRequest) {
+        partial = '';
       }
-      pathMapOptions.push({
-        starIndex,
-        partial: originalRequest,
-        potentials,
-      });
-    } else if (starIndex === pattern.length - 1) {
-      if (originalRequest.startsWith(pattern.slice(0, -1))) {
-        pathMapOptions.push({
-          starIndex,
-          partial: originalRequest.slice(pattern.length - 1),
-          potentials,
-        });
+    } else if (starIndex === 0 && !suffix) {
+      // Everything matches a single wildcard pattern ("*")
+      partial = originalRequest;
+    } else if (!suffix) {
+      // No suffix means the star is at the end of the pattern
+      if (originalRequest.startsWith(prefix)) {
+        partial = originalRequest.slice(prefix.length);
       }
     } else {
-      const [prefix, suffix] = pattern.split('*');
+      // Star was in the middle of the pattern
       if (originalRequest.startsWith(prefix) && originalRequest.endsWith(suffix)) {
-        pathMapOptions.push({
-          starIndex,
-          partial: originalRequest.slice(prefix.length).slice(0, -suffix.length),
-          potentials,
-        });
+        partial = originalRequest.substring(prefix.length, originalRequest.length - suffix.length);
       }
     }
-  }
-
-  if (pathMapOptions.length === 0) {
-    return [];
-  }
 
-  // exact matches take priority then largest prefix match
-  pathMapOptions.sort((a, b) => {
-    if (a.starIndex === -1) {
-      return -1;
-    } else if (b.starIndex === -1) {
-      return 1;
-    } else {
-      return b.starIndex - a.starIndex;
+    // If request was not matched, move on to the next pattern
+    if (partial === undefined) {
+      continue;
     }
-  });
-
-  const replacements: string[] = [];
-  pathMapOptions.forEach((option) => {
-    for (const potential of option.potentials) {
-      let replacement;
-      const starIndex = potential.indexOf('*');
-      if (starIndex === -1) {
-        replacement = potential;
-      } else if (starIndex === potential.length - 1) {
-        replacement = potential.slice(0, -1) + option.partial;
-      } else {
-        const [prefix, suffix] = potential.split('*');
-        replacement = prefix + option.partial + suffix;
+
+    // Create the full replacement values based on the original request and the potentials
+    // for the successfully matched pattern.
+    for (const { hasStar, prefix, suffix } of potentials) {
+      let replacement = prefix;
+
+      if (hasStar) {
+        replacement += partial;
+        if (suffix) {
+          replacement += suffix;
+        }
       }
 
-      replacements.push(replacement);
+      yield replacement;
     }
-  });
-
-  return replacements;
+  }
 }