diff --git a/config/presets/representation-conversion.json b/config/presets/representation-conversion.json
index 475985938c..6f51fbec0c 100644
--- a/config/presets/representation-conversion.json
+++ b/config/presets/representation-conversion.json
@@ -91,12 +91,6 @@
         {
           "@id": "urn:solid-server:default:ContentTypeReplacer"
         },
-        {
-          "@id": "urn:solid-server:default:RdfToQuadConverter"
-        },
-        {
-          "@id": "urn:solid-server:default:QuadToRdfConverter"
-        },
         {
           "@id": "urn:solid-server:default:RdfRepresentationConverter"
         }
diff --git a/src/storage/conversion/ChainedConverter.ts b/src/storage/conversion/ChainedConverter.ts
index fc6de1298a..fda7125ea8 100644
--- a/src/storage/conversion/ChainedConverter.ts
+++ b/src/storage/conversion/ChainedConverter.ts
@@ -1,89 +1,297 @@
 import type { Representation } from '../../ldp/representation/Representation';
+import type { ValuePreference, ValuePreferences } from '../../ldp/representation/RepresentationPreferences';
 import { getLoggerFor } from '../../logging/LogUtil';
-import { InternalServerError } from '../../util/errors/InternalServerError';
-import { matchesMediaType } from './ConversionUtil';
+import { BadRequestHttpError } from '../../util/errors/BadRequestHttpError';
+import { NotImplementedHttpError } from '../../util/errors/NotImplementedHttpError';
+import { cleanPreferences, getBestPreference, getTypeWeight } from './ConversionUtil';
 import type { RepresentationConverterArgs } from './RepresentationConverter';
-import { TypedRepresentationConverter } from './TypedRepresentationConverter';
+import { RepresentationConverter } from './RepresentationConverter';
+import type { TypedRepresentationConverter } from './TypedRepresentationConverter';
+
+type ConverterPreference = ValuePreference & { converter: TypedRepresentationConverter };
+
+/**
+ * A chain of converters that can go from `inTypes` to `outTypes`.
+ * `intermediateTypes` contains the exact types that have the highest weight when going from converter i to i+1.
+ */
+type ConversionPath = {
+  converters: TypedRepresentationConverter[];
+  intermediateTypes: string[];
+  inTypes: ValuePreferences;
+  outTypes: ValuePreferences;
+};
+
+/**
+ * The result of applying a `ConversionPath` to a specific input.
+ */
+type MatchedPath = {
+  path: ConversionPath;
+  inType: string;
+  outType: string;
+  weight: number;
+};
+
+/**
+ * An LRU cache for storing `ConversionPath`s.
+ */
+class LruPathCache {
+  private readonly maxSize: number;
+  // Contents are ordered from least to most recently used
+  private readonly paths: ConversionPath[] = [];
+
+  public constructor(maxSize: number) {
+    this.maxSize = maxSize;
+  }
+
+  /**
+   * Add the given path to the cache as most recently used.
+   */
+  public add(path: ConversionPath): void {
+    this.paths.push(path);
+    if (this.paths.length > this.maxSize) {
+      this.paths.shift();
+    }
+  }
+
+  /**
+   * Find a path that can convert the given type to the given preferences.
+   * Note that this finds the first matching path in the cache,
+   * not the best one, should there be multiple results.
+   * In practice this should almost never be the case though.
+   */
+  public find(inType: string, outPreferences: ValuePreferences): MatchedPath | undefined {
+    // Last element is most recently used so has more chance of being the correct one
+    for (let i = this.paths.length - 1; i >= 0; --i) {
+      const path = this.paths[i];
+      // Check if `inType` matches the input and `outPreferences` the output types of the path
+      const match = this.getMatchedPath(inType, outPreferences, path);
+      if (match) {
+        // Set matched path to most recent result in the cache
+        this.paths.splice(i, 1);
+        this.paths.push(path);
+        return match;
+      }
+    }
+  }
+
+  /**
+   * Calculates the weights and exact types when using the given path on the given type and preferences.
+   * Undefined if there is no match
+   */
+  private getMatchedPath(inType: string, outPreferences: ValuePreferences, path: ConversionPath):
+  MatchedPath | undefined {
+    const inWeight = getTypeWeight(inType, path.inTypes);
+    if (inWeight === 0) {
+      return;
+    }
+    const outMatch = getBestPreference(path.outTypes, outPreferences);
+    if (!outMatch) {
+      return;
+    }
+    return { path, inType, outType: outMatch.value, weight: inWeight * outMatch.weight };
+  }
+}
 
 /**
  * A meta converter that takes an array of other converters as input.
- * It chains these converters by finding intermediate types that are supported by converters on either side.
+ * It chains these converters by finding a path of converters
+ * that can go from the given content-type to the given type preferences.
+ * In case there are multiple paths, the shortest one with the highest weight gets found.
+ * Will error in case no path can be found.
+ *
+ * Generated paths get stored in an internal cache for later re-use on similar requests.
+ * Note that due to this caching `RepresentationConverter`s
+ * that change supported input/output types at runtime are not supported,
+ * unless cache size is set to 0.
+ *
+ * This is not a TypedRepresentationConverter since the supported output types
+ * might depend on what is the input content-type.
+ *
+ * Some suggestions on how this class can be even more optimized should this ever be needed in the future.
+ * Most of these decrease computation time at the cost of more memory.
+ *  - Subpaths that are generated could also be cached.
+ *  - When looking for the next step, cached paths could also be considered.
+ *  - The algorithm could start on both ends of a possible path and work towards the middle.
+ *  - When creating a path, store the list of unused converters instead of checking every step.
  */
-export class ChainedConverter extends TypedRepresentationConverter {
+export class ChainedConverter extends RepresentationConverter {
   protected readonly logger = getLoggerFor(this);
 
   private readonly converters: TypedRepresentationConverter[];
+  private readonly cache: LruPathCache;
 
-  /**
-   * Creates the chain of converters based on the input.
-   * The list of `converters` needs to be at least 2 long.
-   * @param converters - The chain of converters.
-   */
-  public constructor(converters: TypedRepresentationConverter[]) {
+  public constructor(converters: TypedRepresentationConverter[], maxCacheSize = 50) {
     super();
-    if (converters.length < 2) {
-      throw new Error('At least 2 converters are required.');
+    if (converters.length === 0) {
+      throw new Error('At least 1 converter is required.');
     }
     this.converters = [ ...converters ];
-    this.inputTypes = this.first.getInputTypes();
-    this.outputTypes = this.last.getOutputTypes();
+    this.cache = new LruPathCache(maxCacheSize);
   }
 
-  protected get first(): TypedRepresentationConverter {
-    return this.converters[0];
-  }
-
-  protected get last(): TypedRepresentationConverter {
-    return this.converters[this.converters.length - 1];
+  public async canHandle(input: RepresentationConverterArgs): Promise<void> {
+    // Will cache the path if found, and error if not
+    await this.findPath(input);
   }
 
   public async handle(input: RepresentationConverterArgs): Promise<Representation> {
+    const match = await this.findPath(input);
+
+    // No conversion needed
+    if (!this.isMatchedPath(match)) {
+      return input.representation;
+    }
+
+    const { path } = match;
+    this.logger.debug(`Converting ${match.inType} -> ${path.intermediateTypes.join(' -> ')} -> ${match.outType}.`);
+
     const args = { ...input };
-    for (let i = 0; i < this.converters.length - 1; ++i) {
-      const value = await this.getMatchingType(this.converters[i], this.converters[i + 1]);
-      args.preferences = { type: { [value]: 1 }};
-      args.representation = await this.converters[i].handle(args);
+    for (let i = 0; i < path.converters.length - 1; ++i) {
+      const type = path.intermediateTypes[i];
+      args.preferences = { type: { [type]: 1 }};
+      args.representation = await path.converters[i].handle(args);
     }
-    args.preferences = input.preferences;
-    return this.last.handle(args);
+    // For the last converter we set the preferences to the best output type
+    args.preferences = { type: { [match.outType]: 1 }};
+    return path.converters.slice(-1)[0].handle(args);
+  }
+
+  public async handleSafe(input: RepresentationConverterArgs): Promise<Representation> {
+    // This way we don't run `findPath` twice, even though it would be cached for the second call
+    return this.handle(input);
+  }
+
+  private isMatchedPath(path: unknown): path is MatchedPath {
+    return typeof (path as MatchedPath).path === 'object';
   }
 
   /**
-   * Finds the best media type that can be used to chain 2 converters.
+   * Finds a conversion path that can handle the given input,
+   * either in the cache or by generating a new one.
    */
-  protected async getMatchingType(left: TypedRepresentationConverter, right: TypedRepresentationConverter):
-  Promise<string> {
-    const leftTypes = await left.getOutputTypes();
-    const rightTypes = await right.getInputTypes();
-    let bestMatch: { type: string; weight: number } = { type: 'invalid', weight: 0 };
-
-    // Try to find the matching type with the best weight
-    const leftKeys = Object.keys(leftTypes);
-    const rightKeys = Object.keys(rightTypes);
-    for (const leftType of leftKeys) {
-      const leftWeight = leftTypes[leftType];
-      if (leftWeight <= bestMatch.weight) {
-        continue;
-      }
-      for (const rightType of rightKeys) {
-        const rightWeight = rightTypes[rightType];
-        const weight = leftWeight * rightWeight;
-        if (weight > bestMatch.weight && matchesMediaType(leftType, rightType)) {
-          bestMatch = { type: leftType, weight };
-          if (weight === 1) {
-            this.logger.debug(`${bestMatch.type} is an exact match between ${leftKeys} and ${rightKeys}`);
-            return bestMatch.type;
-          }
-        }
+  private async findPath(input: RepresentationConverterArgs): Promise<MatchedPath | ValuePreference> {
+    const type = input.representation.metadata.contentType;
+    if (!type) {
+      throw new BadRequestHttpError('Missing Content-Type header.');
+    }
+    let preferences = input.preferences.type;
+    if (!preferences) {
+      throw new BadRequestHttpError('Missing type preferences.');
+    }
+    preferences = cleanPreferences(preferences);
+
+    const weight = getTypeWeight(type, preferences);
+    if (weight > 0) {
+      this.logger.debug(`No conversion required: ${type} already matches ${Object.keys(input.preferences.type!)}`);
+      return { value: type, weight };
+    }
+
+    // Use a cached solution if we have one.
+    // Note that it's possible that a better one could be generated.
+    // But this is usually highly unlikely.
+    let match = this.cache.find(type, preferences);
+    if (!match) {
+      match = await this.generatePath(type, preferences);
+      this.cache.add(match.path);
+    }
+    return match;
+  }
+
+  /**
+   * Tries to generate the optimal and shortest `ConversionPath` that supports the given parameters,
+   * which will then be used to instantiate a specific `MatchedPath` for those parameters.
+   *
+   * Errors if such a path does not exist.
+   */
+  private async generatePath(inType: string, outPreferences: ValuePreferences): Promise<MatchedPath> {
+    // Generate paths from all converters that match the input type
+    let paths = await this.converters.reduce(async(matches: Promise<ConversionPath[]>, converter):
+    Promise<ConversionPath[]> => {
+      const inTypes = await converter.getInputTypes();
+      if (getTypeWeight(inType, inTypes) > 0) {
+        (await matches).push({
+          converters: [ converter ],
+          intermediateTypes: [],
+          inTypes,
+          outTypes: await converter.getOutputTypes(),
+        });
       }
+      return matches;
+    }, Promise.resolve([]));
+
+    let bestPath = this.findBest(inType, outPreferences, paths);
+    // This will always stop at some point since paths can't have the same converter twice
+    while (!bestPath && paths.length > 0) {
+      // For every path, find all the paths that can be made by adding 1 more converter
+      const promises = paths.map(async(path): Promise<ConversionPath[]> => this.takeStep(path));
+      paths = (await Promise.all(promises)).flat();
+      bestPath = this.findBest(inType, outPreferences, paths);
     }
 
-    if (bestMatch.weight === 0) {
-      this.logger.warn(`No match found between ${leftKeys} and ${rightKeys}`);
-      throw new InternalServerError(`No match found between ${leftKeys} and ${rightKeys}`);
+    if (!bestPath) {
+      this.logger.warn(`No conversion path could be made from ${inType} to ${Object.keys(outPreferences)}.`);
+      throw new NotImplementedHttpError(
+        `No conversion path could be made from ${inType} to ${Object.keys(outPreferences)}.`,
+      );
     }
+    return bestPath;
+  }
+
+  /**
+   * Finds the path from the given list that can convert the given type to the given preferences.
+   * If there are multiple matches the one with the highest result weight gets chosen.
+   * Will return undefined if there are no matches.
+   */
+  private findBest(type: string, preferences: ValuePreferences, paths: ConversionPath[]): MatchedPath | undefined {
+    // Need to use null instead of undefined so `reduce` doesn't take the first element of the array as `best`
+    return paths.reduce((best: MatchedPath | null, path): MatchedPath | null => {
+      const outMatch = getBestPreference(path.outTypes, preferences);
+      if (outMatch && !(best && best.weight >= outMatch.weight)) {
+        // Create new MatchedPath, using the output match above
+        const inWeight = getTypeWeight(type, path.inTypes);
+        return { path, inType: type, outType: outMatch.value, weight: inWeight * outMatch.weight };
+      }
+      return best;
+    }, null) ?? undefined;
+  }
+
+  /**
+   * Finds all converters that could take the output of the given path as input.
+   * For each of these converters a new path gets created which is the input path appended by the converter.
+   */
+  private async takeStep(path: ConversionPath): Promise<ConversionPath[]> {
+    const unusedConverters = this.converters.filter((converter): boolean => !path.converters.includes(converter));
+    const nextConverters = await this.supportedConverters(path.outTypes, unusedConverters);
 
-    this.logger.debug(`${bestMatch.type} is the best match between ${leftKeys} and ${rightKeys}`);
-    return bestMatch.type;
+    // Create a new path for every converter that can be appended
+    return Promise.all(nextConverters.map(async(pref): Promise<ConversionPath> => ({
+      converters: [ ...path.converters, pref.converter ],
+      intermediateTypes: [ ...path.intermediateTypes, pref.value ],
+      inTypes: path.inTypes,
+      outTypes: this.modifyTypeWeights(pref.weight, await pref.converter.getOutputTypes()),
+    })));
+  }
+
+  /**
+   * Creates a new ValuePreferences object, which is equal to the input object
+   * with all values multiplied by the given weight.
+   */
+  private modifyTypeWeights(weight: number, types: ValuePreferences): ValuePreferences {
+    return Object.fromEntries(Object.entries(types).map(([ type, pref ]): [string, number] => [ type, weight * pref ]));
+  }
+
+  /**
+   * Finds all converters in the given list that support taking any of the given types as input.
+   */
+  private async supportedConverters(types: ValuePreferences, converters: TypedRepresentationConverter[]):
+  Promise<ConverterPreference[]> {
+    const promises = converters.map(async(converter): Promise<ConverterPreference | undefined> => {
+      const inputTypes = await converter.getInputTypes();
+      const match = getBestPreference(types, inputTypes);
+      if (match) {
+        return { ...match, converter };
+      }
+    });
+    return (await Promise.all(promises)).filter(Boolean) as ConverterPreference[];
   }
 }
diff --git a/test/integration/GuardedStream.test.ts b/test/integration/GuardedStream.test.ts
index 7db997e260..8ba32961eb 100644
--- a/test/integration/GuardedStream.test.ts
+++ b/test/integration/GuardedStream.test.ts
@@ -4,7 +4,10 @@ import {
   readableToString,
   ChainedConverter,
   guardedStreamFrom,
-  RdfToQuadConverter, BasicRepresentation, getLoggerFor,
+  RdfToQuadConverter,
+  BasicRepresentation,
+  getLoggerFor,
+  INTERNAL_QUADS,
 } from '../../src';
 import type { Representation,
   RepresentationConverterArgs,
@@ -22,16 +25,16 @@ class DummyConverter extends TypedRepresentationConverter {
   }
 
   public async getInputTypes(): Promise<Record<string, number>> {
-    return { '*/*': 1 };
+    return { [INTERNAL_QUADS]: 1 };
   }
 
   public async getOutputTypes(): Promise<Record<string, number>> {
-    return { 'custom/type': 1 };
+    return { 'x/x': 1 };
   }
 
   public async handle({ representation }: RepresentationConverterArgs): Promise<Representation> {
     const data = guardedStreamFrom([ 'dummy' ]);
-    const metadata = new RepresentationMetadata(representation.metadata, 'custom/type');
+    const metadata = new RepresentationMetadata(representation.metadata, 'x/x');
 
     return { binary: true, data, metadata };
   }
@@ -47,7 +50,7 @@ describe('A chained converter where data gets ignored', (): void => {
 
   it('does not throw on async crash.', async(): Promise<void> => {
     jest.useFakeTimers();
-    const result = await converter.handleSafe({ identifier, representation: rep, preferences: {}});
+    const result = await converter.handleSafe({ identifier, representation: rep, preferences: { type: { 'x/x': 1 }}});
 
     expect(await readableToString(result.data)).toBe('dummy');
 
diff --git a/test/unit/storage/conversion/ChainedConverter.test.ts b/test/unit/storage/conversion/ChainedConverter.test.ts
index 7fd7662238..7902ec54a0 100644
--- a/test/unit/storage/conversion/ChainedConverter.test.ts
+++ b/test/unit/storage/conversion/ChainedConverter.test.ts
@@ -1,10 +1,11 @@
 import type { Representation } from '../../../../src/ldp/representation/Representation';
 import { RepresentationMetadata } from '../../../../src/ldp/representation/RepresentationMetadata';
 import type {
-  ValuePreferences,
   RepresentationPreferences,
+  ValuePreferences,
 } from '../../../../src/ldp/representation/RepresentationPreferences';
 import { ChainedConverter } from '../../../../src/storage/conversion/ChainedConverter';
+import { matchesMediaType } from '../../../../src/storage/conversion/ConversionUtil';
 import type { RepresentationConverterArgs } from '../../../../src/storage/conversion/RepresentationConverter';
 import { TypedRepresentationConverter } from '../../../../src/storage/conversion/TypedRepresentationConverter';
 import { CONTENT_TYPE } from '../../../../src/util/Vocabularies';
@@ -28,80 +29,246 @@ class DummyConverter extends TypedRepresentationConverter {
   }
 
   public async handle(input: RepresentationConverterArgs): Promise<Representation> {
+    // Make sure the input type is supported
+    const inType = input.representation.metadata.contentType!;
+    if (!Object.entries(this.inTypes).some(([ range, weight ]): boolean =>
+      weight > 0 && matchesMediaType(range, inType))) {
+      throw new Error(`Unsupported input: ${inType}`);
+    }
+
+    // Make sure we're sending preferences that are actually supported
+    const outType = Object.keys(input.preferences.type!)[0];
+    if (!Object.entries(this.outTypes).some(([ range, weight ]): boolean =>
+      weight > 0 && matchesMediaType(range, outType))) {
+      throw new Error(`Unsupported output: ${outType}`);
+    }
     const metadata = new RepresentationMetadata(input.representation.metadata,
-      { [CONTENT_TYPE]: Object.keys(input.preferences.type!)[0] });
+      { [CONTENT_TYPE]: outType });
     return { ...input.representation, metadata };
   }
 }
 
 describe('A ChainedConverter', (): void => {
-  let converters: TypedRepresentationConverter[];
-  let converter: ChainedConverter;
   let representation: Representation;
   let preferences: RepresentationPreferences;
   let args: RepresentationConverterArgs;
 
   beforeEach(async(): Promise<void> => {
-    converters = [
-      new DummyConverter({ 'text/turtle': 1 }, { 'chain/1': 0.9, 'chain/x': 0.5 }),
-      new DummyConverter({ 'chain/*': 1, 'chain/x': 0.5 }, { 'chain/2': 1 }),
-      new DummyConverter({ 'chain/2': 1 }, { 'internal/quads': 1 }),
-    ];
-    converter = new ChainedConverter(converters);
-
-    const metadata = new RepresentationMetadata('text/turtle');
+    const metadata = new RepresentationMetadata('a/a');
     representation = { metadata } as Representation;
-    preferences = { type: { 'internal/quads': 1 }};
+    preferences = { type: { 'x/x': 1, 'x/*': 0.8 }};
     args = { representation, preferences, identifier: { path: 'path' }};
   });
 
-  it('needs at least 2 converters.', async(): Promise<void> => {
-    expect((): any => new ChainedConverter([])).toThrow('At least 2 converters are required.');
-    expect((): any => new ChainedConverter([ converters[0] ])).toThrow('At least 2 converters are required.');
-    expect(new ChainedConverter([ converters[0], converters[1] ]))
-      .toBeInstanceOf(ChainedConverter);
+  it('needs at least 1 converter.', async(): Promise<void> => {
+    expect((): any => new ChainedConverter([])).toThrow('At least 1 converter is required.');
+    expect(new ChainedConverter([ new DummyConverter({ }, { }) ])).toBeInstanceOf(ChainedConverter);
   });
 
-  it('supports the same inputs as the first converter of the chain.', async(): Promise<void> => {
-    await expect(converter.getInputTypes()).resolves.toEqual(await converters[0].getInputTypes());
+  it('errors if there are no content-type or preferences.', async(): Promise<void> => {
+    args.representation.metadata.contentType = undefined;
+    const converters = [ new DummyConverter({ 'a/a': 1 }, { 'x/x': 1 }) ];
+    const converter = new ChainedConverter(converters);
+    await expect(converter.canHandle(args)).rejects.toThrow('Missing Content-Type header.');
+
+    args.representation.metadata.contentType = 'a/a';
+    args.preferences = { };
+    await expect(converter.canHandle(args)).rejects.toThrow('Missing type preferences.');
   });
 
-  it('supports the same outputs as the last converter of the chain.', async(): Promise<void> => {
-    await expect(converter.getOutputTypes()).resolves.toEqual(await converters[2].getOutputTypes());
+  it('errors if no path can be found.', async(): Promise<void> => {
+    const converters = [ new DummyConverter({ 'a/a': 1 }, { 'x/x': 1 }) ];
+    const converter = new ChainedConverter(converters);
+
+    args.representation.metadata.contentType = 'b/b';
+    await expect(converter.canHandle(args)).rejects
+      .toThrow('No conversion path could be made from b/b to x/x,x/*,internal/*.');
   });
 
-  it('can handle requests with the correct in- and output.', async(): Promise<void> => {
-    await expect(converter.canHandle(args)).resolves.toBeUndefined();
+  it('can handle situations where no conversion is required.', async(): Promise<void> => {
+    const converters = [ new DummyConverter({ 'a/a': 1 }, { 'x/x': 1 }) ];
+    args.representation.metadata.contentType = 'b/b';
+    args.preferences.type = { 'b/*': 0.5 };
+    const converter = new ChainedConverter(converters);
+
+    const result = await converter.handle(args);
+    expect(result.metadata.contentType).toBe('b/b');
   });
 
-  it('errors if the start of the chain does not support the representation type.', async(): Promise<void> => {
-    representation.metadata.contentType = 'bad/type';
-    await expect(converter.canHandle(args)).rejects.toThrow();
+  it('can find paths of length 1.', async(): Promise<void> => {
+    const converters = [ new DummyConverter({ 'a/a': 1 }, { 'x/x': 1 }) ];
+    const converter = new ChainedConverter(converters);
+
+    const result = await converter.handle(args);
+    expect(result.metadata.contentType).toBe('x/x');
   });
 
-  it('errors if the end of the chain does not support the preferences.', async(): Promise<void> => {
-    preferences.type = { 'abc/def': 1 };
-    await expect(converter.canHandle(args)).rejects.toThrow();
+  it('can find longer paths.', async(): Promise<void> => {
+    // Path: a/a -> b/b -> c/c -> x/x
+    const converters = [
+      new DummyConverter({ 'b/b': 0.8, 'b/c': 1 }, { 'c/b': 0.9, 'c/c': 1 }),
+      new DummyConverter({ 'a/a': 0.8, 'a/b': 1 }, { 'b/b': 0.9, 'b/a': 0.5 }),
+      new DummyConverter({ 'd/d': 0.8, 'c/*': 1 }, { 'x/x': 0.9, 'x/a': 1 }),
+    ];
+    const converter = new ChainedConverter(converters);
+
+    const result = await converter.handle(args);
+    expect(result.metadata.contentType).toBe('x/x');
   });
 
-  it('runs the data through the chain.', async(): Promise<void> => {
+  it('will use the best path among the shortest found.', async(): Promise<void> => {
+    // Valid paths: 0 -> 1 -> 2, 3 -> 2, 4 -> 2, 5 -> 2, *6 -> 2*
+    const converters = [
+      new DummyConverter({ 'a/a': 1 }, { 'b/b': 1 }),
+      new DummyConverter({ 'b/b': 1 }, { 'c/c': 1 }),
+      new DummyConverter({ 'c/c': 1 }, { 'x/x': 1 }),
+      new DummyConverter({ '*/*': 0.5 }, { 'c/c': 1 }),
+      new DummyConverter({ 'a/a': 0.8 }, { 'c/c': 1 }),
+      new DummyConverter({ 'a/*': 1 }, { 'c/c': 0.5 }),
+      new DummyConverter({ 'a/a': 1 }, { 'c/c': 0.9 }),
+    ];
+    const converter = new ChainedConverter(converters);
+
+    // Only the best converters should have been called (6 and 2)
+    for (const dummyConverter of converters) {
+      jest.spyOn(dummyConverter, 'handle');
+    }
+    const result = await converter.handle(args);
+    expect(result.metadata.contentType).toBe('x/x');
+    expect(converters[0].handle).toHaveBeenCalledTimes(0);
+    expect(converters[1].handle).toHaveBeenCalledTimes(0);
+    expect(converters[2].handle).toHaveBeenCalledTimes(1);
+    expect(converters[3].handle).toHaveBeenCalledTimes(0);
+    expect(converters[4].handle).toHaveBeenCalledTimes(0);
+    expect(converters[5].handle).toHaveBeenCalledTimes(0);
+    expect(converters[6].handle).toHaveBeenCalledTimes(1);
+  });
+
+  it('will use the intermediate content-types with the best weight.', async(): Promise<void> => {
+    const converters = [
+      new DummyConverter({ 'a/a': 1 }, { 'b/b': 0.8, 'c/c': 0.6 }),
+      new DummyConverter({ 'b/b': 0.1, 'c/*': 0.9 }, { 'd/d': 1, 'e/e': 0.8 }),
+      new DummyConverter({ 'd/*': 0.9, 'e/*': 0.1 }, { 'x/x': 1 }),
+    ];
+    const converter = new ChainedConverter(converters);
+
     jest.spyOn(converters[0], 'handle');
     jest.spyOn(converters[1], 'handle');
-    jest.spyOn(converters[2], 'handle');
-
     const result = await converter.handle(args);
-    expect(result.metadata.contentType).toEqual('internal/quads');
-    expect((converters[0] as any).handle).toHaveBeenCalledTimes(1);
-    expect((converters[1] as any).handle).toHaveBeenCalledTimes(1);
-    expect((converters[2] as any).handle).toHaveBeenCalledTimes(1);
+    expect(result.metadata.contentType).toBe('x/x');
+    let { metadata } = await (converters[0].handle as jest.Mock).mock.results[0].value;
+    expect(metadata.contentType).toBe('c/c');
+    ({ metadata } = await (converters[1].handle as jest.Mock).mock.results[0].value);
+    expect(metadata.contentType).toBe('d/d');
   });
 
-  it('errors if there is no valid chain at runtime.', async(): Promise<void> => {
-    converters = [
-      new DummyConverter({ 'text/turtle': 1 }, { 'chain/1': 0.9, 'chain/x': 0.5 }),
-      new DummyConverter({ 'chain/2': 1 }, { 'internal/quads': 1 }),
+  it('calls handle when calling handleSafe.', async(): Promise<void> => {
+    const converters = [ new DummyConverter({ 'a/a': 1 }, { 'x/x': 1 }) ];
+    const converter = new ChainedConverter(converters);
+    jest.spyOn(converter, 'handle');
+
+    await converter.handleSafe(args);
+    expect(converter.handle).toHaveBeenCalledTimes(1);
+    expect(converter.handle).toHaveBeenLastCalledWith(args);
+  });
+
+  it('caches paths for re-use.', async(): Promise<void> => {
+    const converters = [
+      new DummyConverter({ 'a/a': 0.8 }, { 'b/b': 0.9 }),
+      new DummyConverter({ 'b/b': 0.8 }, { 'x/x': 1 }),
+    ];
+    const converter = new ChainedConverter(converters);
+    let result = await converter.handle(args);
+    expect(result.metadata.contentType).toBe('x/x');
+
+    jest.spyOn(converters[0], 'getInputTypes');
+    jest.spyOn(converters[0], 'getOutputTypes');
+    result = await converter.handle(args);
+    expect(result.metadata.contentType).toBe('x/x');
+    expect(converters[0].getInputTypes).toHaveBeenCalledTimes(0);
+    expect(converters[0].getOutputTypes).toHaveBeenCalledTimes(0);
+  });
+
+  it('removes unused paths from the cache.', async(): Promise<void> => {
+    const converters = [
+      new DummyConverter({ 'a/a': 0.8 }, { 'b/b': 0.9 }),
+      new DummyConverter({ 'b/b': 0.8 }, { 'x/x': 1 }),
+      new DummyConverter({ 'c/c': 0.8 }, { 'b/b': 0.9 }),
+    ];
+    // Cache size 1
+    const converter = new ChainedConverter(converters, 1);
+    let result = await converter.handle(args);
+    expect(result.metadata.contentType).toBe('x/x');
+
+    // Should remove previous path (which contains converter 0)
+    args.representation.metadata.contentType = 'c/c';
+    result = await converter.handle(args);
+    expect(result.metadata.contentType).toBe('x/x');
+
+    jest.spyOn(converters[0], 'getInputTypes');
+    jest.spyOn(converters[0], 'getOutputTypes');
+    args.representation.metadata.contentType = 'a/a';
+    result = await converter.handle(args);
+    expect(result.metadata.contentType).toBe('x/x');
+    expect(converters[0].getInputTypes).not.toHaveBeenCalledTimes(0);
+    expect(converters[0].getOutputTypes).not.toHaveBeenCalledTimes(0);
+  });
+
+  it('keeps the most recently used paths in the cache.', async(): Promise<void> => {
+    const converters = [
+      new DummyConverter({ 'a/a': 1 }, { 'd/d': 1 }),
+      new DummyConverter({ 'b/b': 1 }, { 'd/d': 1 }),
+      new DummyConverter({ 'c/c': 1 }, { 'd/d': 1 }),
+      new DummyConverter({ 'd/d': 1 }, { 'x/x': 1 }),
     ];
-    converter = new ChainedConverter(converters);
-    await expect(converter.handle(args)).rejects.toThrow();
+    // Cache size 2
+    const converter = new ChainedConverter(converters, 2);
+    // Caches path 0
+    await converter.handle(args);
+
+    // Caches path 1
+    args.representation.metadata.contentType = 'b/b';
+    await converter.handle(args);
+
+    // Reset path 0 in cache
+    args.representation.metadata.contentType = 'a/a';
+    await converter.handle(args);
+
+    // Caches path 2 and removes 1
+    args.representation.metadata.contentType = 'c/c';
+    await converter.handle(args);
+
+    jest.spyOn(converters[0], 'getInputTypes');
+    jest.spyOn(converters[1], 'getInputTypes');
+    jest.spyOn(converters[2], 'getInputTypes');
+
+    // Path 0 and 2 should be cached now
+    args.representation.metadata.contentType = 'a/a';
+    await converter.handle(args);
+    expect(converters[0].getInputTypes).toHaveBeenCalledTimes(0);
+    args.representation.metadata.contentType = 'c/c';
+    await converter.handle(args);
+    expect(converters[2].getInputTypes).toHaveBeenCalledTimes(0);
+    args.representation.metadata.contentType = 'b/b';
+    await converter.handle(args);
+    expect(converters[1].getInputTypes).not.toHaveBeenCalledTimes(0);
+  });
+
+  it('does not use cached paths that match content-type but not preferences.', async(): Promise<void> => {
+    const converters = [
+      new DummyConverter({ 'a/a': 1 }, { 'b/b': 1 }),
+      new DummyConverter({ 'b/b': 1 }, { 'x/x': 1 }),
+      new DummyConverter({ 'a/a': 1 }, { 'c/c': 1 }),
+      new DummyConverter({ 'c/c': 1 }, { 'y/y': 1 }),
+    ];
+    const converter = new ChainedConverter(converters);
+
+    // Cache a-b-x path
+    await converter.handle(args);
+
+    // Generate new a-c-y path
+    args.preferences.type = { 'y/y': 1 };
+    const result = await converter.handle(args);
+    expect(result.metadata.contentType).toBe('y/y');
   });
 });