diff --git a/build/webpack/common.js b/build/webpack/common.js
index 58e0845dfeac..d6e620e73e4c 100644
--- a/build/webpack/common.js
+++ b/build/webpack/common.js
@@ -27,6 +27,11 @@ exports.nodeModulesToExternalize = [
     'node-stream-zip',
     'xml2js',
     'vsls/vscode',
+    'pdfkit',
+    'crypto-js',
+    'fontkit',
+    'linebreak',
+    'png-js'
 ];
 exports.nodeModulesToReplacePaths = [
     ...exports.nodeModulesToExternalize
diff --git a/build/webpack/common.ts b/build/webpack/common.ts
index 16ddebb2e869..de762dc824e6 100644
--- a/build/webpack/common.ts
+++ b/build/webpack/common.ts
@@ -29,11 +29,16 @@ export const nodeModulesToExternalize = [
     'node-stream-zip',
     'xml2js',
     'vsls/vscode',
+    'pdfkit',
+    'crypto-js',
+    'fontkit',
+    'linebreak',
+    'png-js'
 ];
 
 export const nodeModulesToReplacePaths = [
     ...nodeModulesToExternalize
-]
+];
 
 export function getDefaultPlugins(name: 'extension' | 'debugger' | 'dependencies' | 'datascience-ui') {
     const plugins = [];
diff --git a/build/webpack/pdfkit.js b/build/webpack/pdfkit.js
new file mode 100644
index 000000000000..5c31590a3924
--- /dev/null
+++ b/build/webpack/pdfkit.js
@@ -0,0 +1,15 @@
+// Copyright (c) Microsoft Corporation. All rights reserved.
+// Licensed under the MIT License.
+
+'use strict';
+
+/*
+This file is only used when using webpack for bundling.
+We have a dummy file so that webpack doesn't fall over when trying to bundle pdfkit.
+Just point it to a dummy file (this file).
+Once webpack is done, we override the pdfkit.js file in the externalized node modules directory
+with the actual source of pdfkit that needs to be used by nodejs (our extension code).
+*/
+
+class PDFDocument {}
+module.exports = PDFDocument;
diff --git a/build/webpack/webpack.extension.config.js b/build/webpack/webpack.extension.config.js
index f559924fdd6b..b19caa9f6a7d 100644
--- a/build/webpack/webpack.extension.config.js
+++ b/build/webpack/webpack.extension.config.js
@@ -11,6 +11,8 @@ const configFileName = path.join(constants_1.ExtensionRootDir, 'tsconfig.extensi
 // Some modules will be pre-genearted and stored in out/.. dir and they'll be referenced via NormalModuleReplacementPlugin
 // We need to ensure they do not get bundled into the output (as they are large).
 const existingModulesInOutDir = common_1.getListOfExistingModulesInOutDir();
+// tslint:disable-next-line:no-var-requires no-require-imports
+const FileManagerPlugin = require('filemanager-webpack-plugin');
 const config = {
     mode: 'production',
     target: 'node',
@@ -49,9 +51,9 @@ const config = {
                     }
                 ]
             },
-            {enforce: 'post', test: /unicode-properties[\/\\]index.js$/, loader: "transform-loader?brfs"},
-            {enforce: 'post', test: /fontkit[\/\\]index.js$/, loader: "transform-loader?brfs"},
-            {enforce: 'post', test: /linebreak[\/\\]src[\/\\]linebreaker.js/, loader: "transform-loader?brfs"}
+            { enforce: 'post', test: /unicode-properties[\/\\]index.js$/, loader: 'transform-loader?brfs' },
+            { enforce: 'post', test: /fontkit[\/\\]index.js$/, loader: 'transform-loader?brfs' },
+            { enforce: 'post', test: /linebreak[\/\\]src[\/\\]linebreaker.js/, loader: 'transform-loader?brfs' }
         ]
     },
     externals: [
@@ -60,9 +62,26 @@ const config = {
         ...existingModulesInOutDir
     ],
     plugins: [
-        ...common_1.getDefaultPlugins('extension')
+        ...common_1.getDefaultPlugins('extension'),
+        // Copy pdfkit bits after extension builds. webpack can't handle pdfkit.
+        new FileManagerPlugin({
+            onEnd: [
+                {
+                    copy: [
+                        { source: './node_modules/pdfkit/js/data/*.*', destination: './out/client/node_modules/data' },
+                        { source: './node_modules/pdfkit/js/pdfkit.js', destination: './out/client/node_modules/' }
+                    ]
+                }
+            ]
+        })
     ],
     resolve: {
+        alias:{
+            // Pointing pdfkit to a dummy js file so webpack doesn't fall over.
+            // Since pdfkit has been externalized (it gets updated with the valid code by copying the pdfkit files
+            // into the right destination).
+            'pdfkit':path.resolve(__dirname, 'pdfkit.js')
+        },
         extensions: ['.ts', '.js'],
         plugins: [
             new tsconfig_paths_webpack_plugin_1.TsconfigPathsPlugin({ configFile: configFileName })
diff --git a/build/webpack/webpack.extension.config.ts b/build/webpack/webpack.extension.config.ts
index 4d9eba1ec88e..9b565d99e369 100644
--- a/build/webpack/webpack.extension.config.ts
+++ b/build/webpack/webpack.extension.config.ts
@@ -16,6 +16,9 @@ const configFileName = path.join(ExtensionRootDir, 'tsconfig.extension.json');
 // We need to ensure they do not get bundled into the output (as they are large).
 const existingModulesInOutDir = getListOfExistingModulesInOutDir();
 
+// tslint:disable-next-line:no-var-requires no-require-imports
+const FileManagerPlugin = require('filemanager-webpack-plugin');
+
 const config: Configuration = {
     mode: 'production',
     target: 'node',
@@ -53,7 +56,11 @@ const config: Configuration = {
                         loader: 'ts-loader'
                     }
                 ]
-            }
+            },
+            {enforce: 'post', test: /unicode-properties[\/\\]index.js$/, loader: 'transform-loader?brfs'},
+            {enforce: 'post', test: /fontkit[\/\\]index.js$/, loader: 'transform-loader?brfs'},
+            {enforce: 'post', test: /pdfkit[\\\/]js[\\\/].*js$/, loader: 'transform-loader?brfs'},
+            {enforce: 'post', test: /linebreak[\/\\]src[\/\\]linebreaker.js/, loader: 'transform-loader?brfs'}
         ]
     },
     externals: [
@@ -62,7 +69,18 @@ const config: Configuration = {
         ...existingModulesInOutDir
     ],
     plugins: [
-        ...getDefaultPlugins('extension')
+        ...getDefaultPlugins('extension'),
+        // Copy pdfkit bits after extension builds. webpack can't handle pdfkit.
+        new FileManagerPlugin({
+            onEnd: [
+                {
+                    copy: [
+                        { source: './node_modules/pdfkit/js/data/*.*', destination: './out/client/node_modules/data' },
+                        { source: './node_modules/pdfkit/js/pdfkit.js', destination: './out/client/node_modules/' }
+                    ]
+                }
+            ]
+        })
     ],
     resolve: {
         extensions: ['.ts', '.js'],
diff --git a/build/webpack/webpack.extension.dependencies.config.js b/build/webpack/webpack.extension.dependencies.config.js
index 5a87744bfcb3..7186a206a71a 100644
--- a/build/webpack/webpack.extension.dependencies.config.js
+++ b/build/webpack/webpack.extension.dependencies.config.js
@@ -2,10 +2,11 @@
 // Licensed under the MIT License.
 'use strict';
 Object.defineProperty(exports, "__esModule", { value: true });
+// tslint:disable-next-line: no-require-imports
+const copyWebpackPlugin = require("copy-webpack-plugin");
 const path = require("path");
 const constants_1 = require("../constants");
 const common_1 = require("./common");
-const copyWebpackPlugin = require("copy-webpack-plugin");
 const entryItems = {};
 common_1.nodeModulesToExternalize.forEach(moduleName => {
     entryItems[`node_modules/${moduleName}`] = `./node_modules/${moduleName}`;
@@ -28,7 +29,10 @@ const config = {
                         loader: path.join(__dirname, 'loaders', 'fixEvalRequire.js')
                     }
                 ]
-            }
+            },
+            { enforce: 'post', test: /unicode-properties[\/\\]index.js$/, loader: 'transform-loader?brfs' },
+            { enforce: 'post', test: /fontkit[\/\\]index.js$/, loader: 'transform-loader?brfs' },
+            { enforce: 'post', test: /linebreak[\/\\]src[\/\\]linebreaker.js/, loader: 'transform-loader?brfs' }
         ]
     },
     externals: [
@@ -48,6 +52,12 @@ const config = {
         ])
     ],
     resolve: {
+        alias:{
+            // Pointing pdfkit to a dummy js file so webpack doesn't fall over.
+            // Since pdfkit has been externalized (it gets updated with the valid code by copying the pdfkit files
+            // into the right destination).
+            'pdfkit':path.resolve(__dirname, 'pdfkit.js')
+        },
         extensions: ['.js']
     },
     output: {
diff --git a/build/webpack/webpack.extension.dependencies.config.ts b/build/webpack/webpack.extension.dependencies.config.ts
index 76c72bea9fba..f380ac8a77e6 100644
--- a/build/webpack/webpack.extension.dependencies.config.ts
+++ b/build/webpack/webpack.extension.dependencies.config.ts
@@ -3,11 +3,12 @@
 
 'use strict';
 
+// tslint:disable-next-line: no-require-imports
+import copyWebpackPlugin = require('copy-webpack-plugin');
 import * as path from 'path';
 import * as webpack from 'webpack';
 import { ExtensionRootDir } from '../constants';
 import { getDefaultPlugins, nodeModulesToExternalize } from './common';
-import copyWebpackPlugin = require('copy-webpack-plugin');
 
 const entryItems: Record<string, string> = {};
 nodeModulesToExternalize.forEach(moduleName => {
@@ -32,7 +33,11 @@ const config: webpack.Configuration = {
                         loader: path.join(__dirname, 'loaders', 'fixEvalRequire.js')
                     }
                 ]
-            }            
+            },
+            {enforce: 'post', test: /unicode-properties[\/\\]index.js$/, loader: 'transform-loader?brfs'},
+            {enforce: 'post', test: /fontkit[\/\\]index.js$/, loader: 'transform-loader?brfs'},
+            {enforce: 'post', test: /pdfkit[\\\/]js[\\\/].*js$/, loader: 'transform-loader?brfs'},
+            {enforce: 'post', test: /linebreak[\/\\]src[\/\\]linebreaker.js/, loader: 'transform-loader?brfs'}
         ]
     },
     externals: [
diff --git a/news/2 Fixes/6277.md b/news/2 Fixes/6277.md
new file mode 100644
index 000000000000..03b333fff46e
--- /dev/null
+++ b/news/2 Fixes/6277.md	
@@ -0,0 +1 @@
+Fix pdf export in release bits.
\ No newline at end of file
diff --git a/package-lock.json b/package-lock.json
index f3c5cf528f37..15c526c350ea 100644
--- a/package-lock.json
+++ b/package-lock.json
@@ -2644,6 +2644,60 @@
             "resolved": "https://registry.npmjs.org/arch/-/arch-2.1.0.tgz",
             "integrity": "sha1-NhOqRhSQZLPB8GB5Gb8dR4boKIk="
         },
+        "archiver": {
+            "version": "3.0.0",
+            "resolved": "https://registry.npmjs.org/archiver/-/archiver-3.0.0.tgz",
+            "integrity": "sha512-5QeR6Xc5hSA9X1rbQfcuQ6VZuUXOaEdB65Dhmk9duuRJHYif/ZyJfuyJqsQrj34PFjU5emv5/MmfgA8un06onw==",
+            "dev": true,
+            "requires": {
+                "archiver-utils": "^2.0.0",
+                "async": "^2.0.0",
+                "buffer-crc32": "^0.2.1",
+                "glob": "^7.0.0",
+                "readable-stream": "^2.0.0",
+                "tar-stream": "^1.5.0",
+                "zip-stream": "^2.0.1"
+            },
+            "dependencies": {
+                "async": {
+                    "version": "2.6.2",
+                    "resolved": "https://registry.npmjs.org/async/-/async-2.6.2.tgz",
+                    "integrity": "sha512-H1qVYh1MYhEEFLsP97cVKqCGo7KfCyTt6uEWqsTBr9SO84oK9Uwbyd/yCW+6rKJLHksBNUVWZDAjfS+Ccx0Bbg==",
+                    "dev": true,
+                    "requires": {
+                        "lodash": "^4.17.11"
+                    }
+                }
+            }
+        },
+        "archiver-utils": {
+            "version": "2.0.0",
+            "resolved": "https://registry.npmjs.org/archiver-utils/-/archiver-utils-2.0.0.tgz",
+            "integrity": "sha512-JRBgcVvDX4Mwu2RBF8bBaHcQCSxab7afsxAPYDQ5W+19quIPP5CfKE7Ql+UHs9wYvwsaNR8oDuhtf5iqrKmzww==",
+            "dev": true,
+            "requires": {
+                "glob": "^7.0.0",
+                "graceful-fs": "^4.1.0",
+                "lazystream": "^1.0.0",
+                "lodash.assign": "^4.2.0",
+                "lodash.defaults": "^4.2.0",
+                "lodash.difference": "^4.5.0",
+                "lodash.flatten": "^4.4.0",
+                "lodash.isplainobject": "^4.0.6",
+                "lodash.toarray": "^4.4.0",
+                "lodash.union": "^4.6.0",
+                "normalize-path": "^3.0.0",
+                "readable-stream": "^2.0.0"
+            },
+            "dependencies": {
+                "normalize-path": {
+                    "version": "3.0.0",
+                    "resolved": "https://registry.npmjs.org/normalize-path/-/normalize-path-3.0.0.tgz",
+                    "integrity": "sha512-6eZs5Ls3WtCisHWp9S2GUy8dqkpGi4BVSz3GaqiE6ezub0512ESztXUwUB6C6IKbQkY2Pnb/mD4WYojCRwcwLA==",
+                    "dev": true
+                }
+            }
+        },
         "archy": {
             "version": "1.0.0",
             "resolved": "https://registry.npmjs.org/archy/-/archy-1.0.0.tgz",
@@ -5170,6 +5224,18 @@
             "integrity": "sha1-E3kY1teCg/ffemt8WmPhQOaUJeY=",
             "dev": true
         },
+        "compress-commons": {
+            "version": "1.2.2",
+            "resolved": "https://registry.npmjs.org/compress-commons/-/compress-commons-1.2.2.tgz",
+            "integrity": "sha1-UkqfEJA/OoEzibAiXSfEi7dRiQ8=",
+            "dev": true,
+            "requires": {
+                "buffer-crc32": "^0.2.1",
+                "crc32-stream": "^2.0.0",
+                "normalize-path": "^2.0.0",
+                "readable-stream": "^2.0.0"
+            }
+        },
         "concat-map": {
             "version": "0.0.1",
             "resolved": "https://registry.npmjs.org/concat-map/-/concat-map-0.0.1.tgz",
@@ -5425,6 +5491,189 @@
                 }
             }
         },
+        "cpx": {
+            "version": "1.5.0",
+            "resolved": "https://registry.npmjs.org/cpx/-/cpx-1.5.0.tgz",
+            "integrity": "sha1-GFvgGFEdhycN7czCkxceN2VauI8=",
+            "dev": true,
+            "requires": {
+                "babel-runtime": "^6.9.2",
+                "chokidar": "^1.6.0",
+                "duplexer": "^0.1.1",
+                "glob": "^7.0.5",
+                "glob2base": "^0.0.12",
+                "minimatch": "^3.0.2",
+                "mkdirp": "^0.5.1",
+                "resolve": "^1.1.7",
+                "safe-buffer": "^5.0.1",
+                "shell-quote": "^1.6.1",
+                "subarg": "^1.0.0"
+            },
+            "dependencies": {
+                "anymatch": {
+                    "version": "1.3.2",
+                    "resolved": "https://registry.npmjs.org/anymatch/-/anymatch-1.3.2.tgz",
+                    "integrity": "sha512-0XNayC8lTHQ2OI8aljNCN3sSx6hsr/1+rlcDAotXJR7C1oZZHCNsfpbKwMjRA3Uqb5tF1Rae2oloTr4xpq+WjA==",
+                    "dev": true,
+                    "requires": {
+                        "micromatch": "^2.1.5",
+                        "normalize-path": "^2.0.0"
+                    }
+                },
+                "arr-diff": {
+                    "version": "2.0.0",
+                    "resolved": "https://registry.npmjs.org/arr-diff/-/arr-diff-2.0.0.tgz",
+                    "integrity": "sha1-jzuCf5Vai9ZpaX5KQlasPOrjVs8=",
+                    "dev": true,
+                    "requires": {
+                        "arr-flatten": "^1.0.1"
+                    }
+                },
+                "array-unique": {
+                    "version": "0.2.1",
+                    "resolved": "https://registry.npmjs.org/array-unique/-/array-unique-0.2.1.tgz",
+                    "integrity": "sha1-odl8yvy8JiXMcPrc6zalDFiwGlM=",
+                    "dev": true
+                },
+                "braces": {
+                    "version": "1.8.5",
+                    "resolved": "https://registry.npmjs.org/braces/-/braces-1.8.5.tgz",
+                    "integrity": "sha1-uneWLhLf+WnWt2cR6RS3N4V79qc=",
+                    "dev": true,
+                    "requires": {
+                        "expand-range": "^1.8.1",
+                        "preserve": "^0.2.0",
+                        "repeat-element": "^1.1.2"
+                    }
+                },
+                "chokidar": {
+                    "version": "1.7.0",
+                    "resolved": "https://registry.npmjs.org/chokidar/-/chokidar-1.7.0.tgz",
+                    "integrity": "sha1-eY5ol3gVHIB2tLNg5e3SjNortGg=",
+                    "dev": true,
+                    "requires": {
+                        "anymatch": "^1.3.0",
+                        "async-each": "^1.0.0",
+                        "fsevents": "^1.0.0",
+                        "glob-parent": "^2.0.0",
+                        "inherits": "^2.0.1",
+                        "is-binary-path": "^1.0.0",
+                        "is-glob": "^2.0.0",
+                        "path-is-absolute": "^1.0.0",
+                        "readdirp": "^2.0.0"
+                    }
+                },
+                "expand-brackets": {
+                    "version": "0.1.5",
+                    "resolved": "https://registry.npmjs.org/expand-brackets/-/expand-brackets-0.1.5.tgz",
+                    "integrity": "sha1-3wcoTjQqgHzXM6xa9yQR5YHRF3s=",
+                    "dev": true,
+                    "requires": {
+                        "is-posix-bracket": "^0.1.0"
+                    }
+                },
+                "extglob": {
+                    "version": "0.3.2",
+                    "resolved": "https://registry.npmjs.org/extglob/-/extglob-0.3.2.tgz",
+                    "integrity": "sha1-Lhj/PS9JqydlzskCPwEdqo2DSaE=",
+                    "dev": true,
+                    "requires": {
+                        "is-extglob": "^1.0.0"
+                    }
+                },
+                "glob-parent": {
+                    "version": "2.0.0",
+                    "resolved": "https://registry.npmjs.org/glob-parent/-/glob-parent-2.0.0.tgz",
+                    "integrity": "sha1-gTg9ctsFT8zPUzbaqQLxgvbtuyg=",
+                    "dev": true,
+                    "requires": {
+                        "is-glob": "^2.0.0"
+                    }
+                },
+                "is-extglob": {
+                    "version": "1.0.0",
+                    "resolved": "https://registry.npmjs.org/is-extglob/-/is-extglob-1.0.0.tgz",
+                    "integrity": "sha1-rEaBd8SUNAWgkvyPKXYMb/xiBsA=",
+                    "dev": true
+                },
+                "is-glob": {
+                    "version": "2.0.1",
+                    "resolved": "https://registry.npmjs.org/is-glob/-/is-glob-2.0.1.tgz",
+                    "integrity": "sha1-0Jb5JqPe1WAPP9/ZEZjLCIjC2GM=",
+                    "dev": true,
+                    "requires": {
+                        "is-extglob": "^1.0.0"
+                    }
+                },
+                "kind-of": {
+                    "version": "3.2.2",
+                    "resolved": "https://registry.npmjs.org/kind-of/-/kind-of-3.2.2.tgz",
+                    "integrity": "sha1-MeohpzS6ubuw8yRm2JOupR5KPGQ=",
+                    "dev": true,
+                    "requires": {
+                        "is-buffer": "^1.1.5"
+                    }
+                },
+                "micromatch": {
+                    "version": "2.3.11",
+                    "resolved": "https://registry.npmjs.org/micromatch/-/micromatch-2.3.11.tgz",
+                    "integrity": "sha1-hmd8l9FyCzY0MdBNDRUpO9OMFWU=",
+                    "dev": true,
+                    "requires": {
+                        "arr-diff": "^2.0.0",
+                        "array-unique": "^0.2.1",
+                        "braces": "^1.8.2",
+                        "expand-brackets": "^0.1.4",
+                        "extglob": "^0.3.1",
+                        "filename-regex": "^2.0.0",
+                        "is-extglob": "^1.0.0",
+                        "is-glob": "^2.0.1",
+                        "kind-of": "^3.0.2",
+                        "normalize-path": "^2.0.1",
+                        "object.omit": "^2.0.0",
+                        "parse-glob": "^3.0.4",
+                        "regex-cache": "^0.4.2"
+                    }
+                }
+            }
+        },
+        "crc": {
+            "version": "3.8.0",
+            "resolved": "https://registry.npmjs.org/crc/-/crc-3.8.0.tgz",
+            "integrity": "sha512-iX3mfgcTMIq3ZKLIsVFAbv7+Mc10kxabAGQb8HvjA1o3T1PIYprbakQ65d3I+2HGHt6nSKkM9PYjgoJO2KcFBQ==",
+            "dev": true,
+            "requires": {
+                "buffer": "^5.1.0"
+            },
+            "dependencies": {
+                "base64-js": {
+                    "version": "1.3.0",
+                    "resolved": "https://registry.npmjs.org/base64-js/-/base64-js-1.3.0.tgz",
+                    "integrity": "sha512-ccav/yGvoa80BQDljCxsmmQ3Xvx60/UpBIij5QN21W3wBi/hhIC9OoO+KLpu9IJTS9j4DRVJ3aDDF9cMSoa2lw==",
+                    "dev": true
+                },
+                "buffer": {
+                    "version": "5.2.1",
+                    "resolved": "https://registry.npmjs.org/buffer/-/buffer-5.2.1.tgz",
+                    "integrity": "sha512-c+Ko0loDaFfuPWiL02ls9Xd3GO3cPVmUobQ6t3rXNUk304u6hGq+8N/kFi+QEIKhzK3uwolVhLzszmfLmMLnqg==",
+                    "dev": true,
+                    "requires": {
+                        "base64-js": "^1.0.2",
+                        "ieee754": "^1.1.4"
+                    }
+                }
+            }
+        },
+        "crc32-stream": {
+            "version": "2.0.0",
+            "resolved": "https://registry.npmjs.org/crc32-stream/-/crc32-stream-2.0.0.tgz",
+            "integrity": "sha1-483TtN8xaN10494/u8t7KX/pCPQ=",
+            "dev": true,
+            "requires": {
+                "crc": "^3.4.4",
+                "readable-stream": "^2.0.0"
+            }
+        },
         "create-ecdh": {
             "version": "4.0.3",
             "resolved": "https://registry.npmjs.org/create-ecdh/-/create-ecdh-4.0.3.tgz",
@@ -7120,6 +7369,57 @@
                 }
             }
         },
+        "expand-range": {
+            "version": "1.8.2",
+            "resolved": "https://registry.npmjs.org/expand-range/-/expand-range-1.8.2.tgz",
+            "integrity": "sha1-opnv/TNf4nIeuujiV+x5ZE/IUzc=",
+            "dev": true,
+            "requires": {
+                "fill-range": "^2.1.0"
+            },
+            "dependencies": {
+                "fill-range": {
+                    "version": "2.2.4",
+                    "resolved": "https://registry.npmjs.org/fill-range/-/fill-range-2.2.4.tgz",
+                    "integrity": "sha512-cnrcCbj01+j2gTG921VZPnHbjmdAf8oQV/iGeV2kZxGSyfYjjTyY79ErsK1WJWMpw6DaApEX72binqJE+/d+5Q==",
+                    "dev": true,
+                    "requires": {
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+                        "universalify": "^0.1.0"
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@@ -7528,6 +7861,12 @@
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+            "resolved": "https://registry.npmjs.org/find-index/-/find-index-0.1.1.tgz",
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@@ -8588,6 +8927,42 @@
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+            "requires": {
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@@ -8702,6 +9077,15 @@
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+            "resolved": "https://registry.npmjs.org/glob2base/-/glob2base-0.0.12.tgz",
+            "integrity": "sha1-nUGbPijxLoOjYhZKJ3BVkiycDVY=",
+            "dev": true,
+            "requires": {
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@@ -10183,6 +10567,21 @@
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+            "resolved": "https://registry.npmjs.org/is-dotfile/-/is-dotfile-1.0.3.tgz",
+            "integrity": "sha1-pqLzL/0t+wT1yiXs0Pa4PPeYoeE=",
+            "dev": true
+        },
+        "is-equal-shallow": {
+            "version": "0.1.3",
+            "resolved": "https://registry.npmjs.org/is-equal-shallow/-/is-equal-shallow-0.1.3.tgz",
+            "integrity": "sha1-IjgJj8Ih3gvPpdnqxMRdY4qhxTQ=",
+            "dev": true,
+            "requires": {
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+            }
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@@ -10316,6 +10715,18 @@
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+        "is-posix-bracket": {
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+            "resolved": "https://registry.npmjs.org/is-posix-bracket/-/is-posix-bracket-0.1.1.tgz",
+            "integrity": "sha1-MzTceXdDaOkvAW5vvAqI9c1ua8Q=",
+            "dev": true
+        },
+        "is-primitive": {
+            "version": "2.0.0",
+            "resolved": "https://registry.npmjs.org/is-primitive/-/is-primitive-2.0.0.tgz",
+            "integrity": "sha1-IHurkWOEmcB7Kt8kCkGochADRXU=",
+            "dev": true
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@@ -11551,6 +11962,12 @@
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+        "lodash.assign": {
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+            "integrity": "sha1-DZnzzNem0mHRm9rrkkUAXShYCOc=",
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@@ -11569,6 +11986,18 @@
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+            "integrity": "sha1-0JF4cW/+pN3p5ft7N/bwgCJ0WAw=",
+            "dev": true
+        },
+        "lodash.difference": {
+            "version": "4.5.0",
+            "resolved": "https://registry.npmjs.org/lodash.difference/-/lodash.difference-4.5.0.tgz",
+            "integrity": "sha1-nMtOUF1Ia5FlE0V3KIWi3yf9AXw=",
+            "dev": true
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         "lodash.flatten": {
             "version": "4.4.0",
             "resolved": "https://registry.npmjs.org/lodash.flatten/-/lodash.flatten-4.4.0.tgz",
@@ -11599,6 +12028,12 @@
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             "dev": true
         },
+        "lodash.isplainobject": {
+            "version": "4.0.6",
+            "resolved": "https://registry.npmjs.org/lodash.isplainobject/-/lodash.isplainobject-4.0.6.tgz",
+            "integrity": "sha1-fFJqUtibRcRcxpC4gWO+BJf1UMs=",
+            "dev": true
+        },
         "lodash.set": {
             "version": "4.3.2",
             "resolved": "https://registry.npmjs.org/lodash.set/-/lodash.set-4.3.2.tgz",
@@ -11623,6 +12058,18 @@
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             "dev": true
         },
+        "lodash.toarray": {
+            "version": "4.4.0",
+            "resolved": "https://registry.npmjs.org/lodash.toarray/-/lodash.toarray-4.4.0.tgz",
+            "integrity": "sha1-JMS/zWsvuji/0FlNsRedjptlZWE=",
+            "dev": true
+        },
+        "lodash.union": {
+            "version": "4.6.0",
+            "resolved": "https://registry.npmjs.org/lodash.union/-/lodash.union-4.6.0.tgz",
+            "integrity": "sha1-SLtQiECfFvGCFmZkHETdGqrjzYg=",
+            "dev": true
+        },
         "lodash.uniq": {
             "version": "4.5.0",
             "resolved": "https://registry.npmjs.org/lodash.uniq/-/lodash.uniq-4.5.0.tgz",
@@ -11863,6 +12310,12 @@
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             "dev": true
         },
+        "math-random": {
+            "version": "1.0.4",
+            "resolved": "https://registry.npmjs.org/math-random/-/math-random-1.0.4.tgz",
+            "integrity": "sha512-rUxjysqif/BZQH2yhd5Aaq7vXMSx9NdEsQcyA07uEzIvxgI7zIr33gGsh+RU0/XjmQpCW7RsVof1vlkvQVCK5A==",
+            "dev": true
+        },
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@@ -12531,6 +12984,41 @@
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             "dev": true
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+        "mv": {
+            "version": "2.1.1",
+            "resolved": "https://registry.npmjs.org/mv/-/mv-2.1.1.tgz",
+            "integrity": "sha1-rmzg1vbV4KT32JN5jQPB6pVZtqI=",
+            "dev": true,
+            "requires": {
+                "mkdirp": "~0.5.1",
+                "ncp": "~2.0.0",
+                "rimraf": "~2.4.0"
+            },
+            "dependencies": {
+                "glob": {
+                    "version": "6.0.4",
+                    "resolved": "https://registry.npmjs.org/glob/-/glob-6.0.4.tgz",
+                    "integrity": "sha1-DwiGD2oVUSey+t1PnOJLGqtuTSI=",
+                    "dev": true,
+                    "requires": {
+                        "inflight": "^1.0.4",
+                        "inherits": "2",
+                        "minimatch": "2 || 3",
+                        "once": "^1.3.0",
+                        "path-is-absolute": "^1.0.0"
+                    }
+                },
+                "rimraf": {
+                    "version": "2.4.5",
+                    "resolved": "https://registry.npmjs.org/rimraf/-/rimraf-2.4.5.tgz",
+                    "integrity": "sha1-7nEM5dk6j9uFb7Xqj/Di11k0sto=",
+                    "dev": true,
+                    "requires": {
+                        "glob": "^6.0.1"
+                    }
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+            }
+        },
         "named-js-regexp": {
             "version": "1.3.3",
             "resolved": "https://registry.npmjs.org/named-js-regexp/-/named-js-regexp-1.3.3.tgz",
@@ -12562,6 +13050,12 @@
                 "to-regex": "^3.0.1"
             }
         },
+        "ncp": {
+            "version": "2.0.0",
+            "resolved": "https://registry.npmjs.org/ncp/-/ncp-2.0.0.tgz",
+            "integrity": "sha1-GVoh1sRuNh0vsSgbo4uR6d9727M=",
+            "dev": true
+        },
         "nearley": {
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             "resolved": "https://registry.npmjs.org/nearley/-/nearley-2.15.1.tgz",
@@ -13358,6 +13852,27 @@
                 "make-iterator": "^1.0.0"
             }
         },
+        "object.omit": {
+            "version": "2.0.1",
+            "resolved": "https://registry.npmjs.org/object.omit/-/object.omit-2.0.1.tgz",
+            "integrity": "sha1-Gpx0SCnznbuFjHbKNXmuKlTr0fo=",
+            "dev": true,
+            "requires": {
+                "for-own": "^0.1.4",
+                "is-extendable": "^0.1.1"
+            },
+            "dependencies": {
+                "for-own": {
+                    "version": "0.1.5",
+                    "resolved": "https://registry.npmjs.org/for-own/-/for-own-0.1.5.tgz",
+                    "integrity": "sha1-UmXGgaTylNq78XyVCbZ2OqhFEM4=",
+                    "dev": true,
+                    "requires": {
+                        "for-in": "^1.0.1"
+                    }
+                }
+            }
+        },
         "object.pick": {
             "version": "1.3.0",
             "resolved": "https://registry.npmjs.org/object.pick/-/object.pick-1.3.0.tgz",
@@ -13745,6 +14260,35 @@
                 "path-root": "^0.1.1"
             }
         },
+        "parse-glob": {
+            "version": "3.0.4",
+            "resolved": "https://registry.npmjs.org/parse-glob/-/parse-glob-3.0.4.tgz",
+            "integrity": "sha1-ssN2z7EfNVE7rdFz7wu246OIORw=",
+            "dev": true,
+            "requires": {
+                "glob-base": "^0.3.0",
+                "is-dotfile": "^1.0.0",
+                "is-extglob": "^1.0.0",
+                "is-glob": "^2.0.0"
+            },
+            "dependencies": {
+                "is-extglob": {
+                    "version": "1.0.0",
+                    "resolved": "https://registry.npmjs.org/is-extglob/-/is-extglob-1.0.0.tgz",
+                    "integrity": "sha1-rEaBd8SUNAWgkvyPKXYMb/xiBsA=",
+                    "dev": true
+                },
+                "is-glob": {
+                    "version": "2.0.1",
+                    "resolved": "https://registry.npmjs.org/is-glob/-/is-glob-2.0.1.tgz",
+                    "integrity": "sha1-0Jb5JqPe1WAPP9/ZEZjLCIjC2GM=",
+                    "dev": true,
+                    "requires": {
+                        "is-extglob": "^1.0.0"
+                    }
+                }
+            }
+        },
         "parse-json": {
             "version": "2.2.0",
             "resolved": "https://registry.npmjs.org/parse-json/-/parse-json-2.2.0.tgz",
@@ -14186,6 +14730,12 @@
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             "dev": true
         },
+        "preserve": {
+            "version": "0.2.0",
+            "resolved": "https://registry.npmjs.org/preserve/-/preserve-0.2.0.tgz",
+            "integrity": "sha1-gV7R9uvGWSb4ZbMQwHE7yzMVzks=",
+            "dev": true
+        },
         "pretty-error": {
             "version": "2.1.1",
             "resolved": "https://registry.npmjs.org/pretty-error/-/pretty-error-2.1.1.tgz",
@@ -14426,6 +14976,25 @@
                 "ret": "~0.1.10"
             }
         },
+        "randomatic": {
+            "version": "3.1.1",
+            "resolved": "https://registry.npmjs.org/randomatic/-/randomatic-3.1.1.tgz",
+            "integrity": "sha512-TuDE5KxZ0J461RVjrJZCJc+J+zCkTb1MbH9AQUq68sMhOMcy9jLcb3BrZKgp9q9Ncltdg4QVqWrH02W2EFFVYw==",
+            "dev": true,
+            "requires": {
+                "is-number": "^4.0.0",
+                "kind-of": "^6.0.0",
+                "math-random": "^1.0.1"
+            },
+            "dependencies": {
+                "is-number": {
+                    "version": "4.0.0",
+                    "resolved": "https://registry.npmjs.org/is-number/-/is-number-4.0.0.tgz",
+                    "integrity": "sha512-rSklcAIlf1OmFdyAqbnWTLVelsQ58uvZ66S/ZyawjWqIviTWCjg2PzVGw8WUA+nNuPTqb4wgA+NszrJ+08LlgQ==",
+                    "dev": true
+                }
+            }
+        },
         "randombytes": {
             "version": "2.0.6",
             "resolved": "https://registry.npmjs.org/randombytes/-/randombytes-2.0.6.tgz",
@@ -14938,6 +15507,15 @@
                 "private": "^0.1.6"
             }
         },
+        "regex-cache": {
+            "version": "0.4.4",
+            "resolved": "https://registry.npmjs.org/regex-cache/-/regex-cache-0.4.4.tgz",
+            "integrity": "sha512-nVIZwtCjkC9YgvWkpM55B5rBhBYRZhAaJbgcFYXXsHnbZ9UZI9nnVWYZpBlCqv9ho2eZryPnWrZGsOdPwVWXWQ==",
+            "dev": true,
+            "requires": {
+                "is-equal-shallow": "^0.1.3"
+            }
+        },
         "regex-not": {
             "version": "1.0.2",
             "resolved": "https://registry.npmjs.org/regex-not/-/regex-not-1.0.2.tgz",
@@ -16634,6 +17212,15 @@
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             "dev": true
         },
+        "subarg": {
+            "version": "1.0.0",
+            "resolved": "https://registry.npmjs.org/subarg/-/subarg-1.0.0.tgz",
+            "integrity": "sha1-9izxdYHplrSPyWVpn1TAauJouNI=",
+            "dev": true,
+            "requires": {
+                "minimist": "^1.1.0"
+            }
+        },
         "sudo-prompt": {
             "version": "8.2.0",
             "resolved": "https://registry.npmjs.org/sudo-prompt/-/sudo-prompt-8.2.0.tgz",
@@ -19978,6 +20565,17 @@
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             "dev": true
         },
+        "zip-stream": {
+            "version": "2.0.1",
+            "resolved": "https://registry.npmjs.org/zip-stream/-/zip-stream-2.0.1.tgz",
+            "integrity": "sha512-c+eUhhkDpaK87G/py74wvWLtz2kzMPNCCkUApkun50ssE0oQliIQzWpTnwjB+MTKVIf2tGzIgHyqW/Y+W77ecQ==",
+            "dev": true,
+            "requires": {
+                "archiver-utils": "^2.0.0",
+                "compress-commons": "^1.2.0",
+                "readable-stream": "^2.0.0"
+            }
+        },
         "zone.js": {
             "version": "0.7.6",
             "resolved": "https://registry.npmjs.org/zone.js/-/zone.js-0.7.6.tgz",
diff --git a/package.json b/package.json
index e98f51f10bd8..b202aaa3bb22 100644
--- a/package.json
+++ b/package.json
@@ -2336,6 +2336,7 @@
         "event-stream": "3.3.4",
         "expose-loader": "^0.7.5",
         "file-loader": "^2.0.0",
+        "filemanager-webpack-plugin": "^2.0.5",
         "flat": "^4.0.0",
         "gulp": "^4.0.0",
         "gulp-azure-storage": "^0.9.0",
diff --git a/package.nls.json b/package.nls.json
index c5af11a52d0d..2bd9ebdb872c 100644
--- a/package.nls.json
+++ b/package.nls.json
@@ -273,5 +273,6 @@
     "DataScience.editSection" : "Input new cells here.",
     "DataScience.restartKernelMessageDontAskAgain" : "Yes, and Don't Ask Again",
     "DataScience.selectedImageListLabel" : "Selected Image",
-    "DataScience.imageListLabel" : "Image"
+    "DataScience.imageListLabel" : "Image",
+    "DataScience.exportImageFailed" : "Error exporting image: {0}"
 }
diff --git a/src/client/common/utils/localize.ts b/src/client/common/utils/localize.ts
index cc4d5096c446..621f5e328141 100644
--- a/src/client/common/utils/localize.ts
+++ b/src/client/common/utils/localize.ts
@@ -202,6 +202,7 @@ export namespace DataScience {
     export const editSection = localize('DataScience.editSection', 'Input new cells here.');
     export const selectedImageListLabel = localize('DataScience.selectedImageListLabel', 'Selected Image');
     export const imageListLabel = localize('DataScience.imageListLabel', 'Image');
+    export const exportImageFailed = localize('DataScience.exportImageFailed', 'Error exporting image: {0}');
 }
 
 export namespace DebugConfigStrings {
diff --git a/src/client/datascience/plotting/plotViewer.ts b/src/client/datascience/plotting/plotViewer.ts
index 0b8c5504ff89..bc040601a0cf 100644
--- a/src/client/datascience/plotting/plotViewer.ts
+++ b/src/client/datascience/plotting/plotViewer.ts
@@ -5,11 +5,13 @@ import '../../common/extensions';
 
 import { inject, injectable } from 'inversify';
 import * as path from 'path';
-import * as pdfkit from 'pdfkit';
 import { Event, EventEmitter, ViewColumn } from 'vscode';
 
+import { traceInfo } from '../../../client/common/logger';
+import { createDeferred } from '../../../client/common/utils/async';
 import { IApplicationShell, IWebPanelProvider, IWorkspaceService } from '../../common/application/types';
 import { EXTENSION_ROOT_DIR } from '../../common/constants';
+import { traceError } from '../../common/logger';
 import { IFileSystem } from '../../common/platform/types';
 import { IConfigurationService, IDisposable } from '../../common/types';
 import * as localize from '../../common/utils/localize';
@@ -113,7 +115,7 @@ export class PlotViewer extends WebViewHost<IPlotViewerMapping> implements IPlot
     }
 
     private async exportPlot(payload: IExportPlotRequest) : Promise<void> {
-
+        traceInfo('exporting plot...');
         const filtersObject: Record<string, string[]> = {};
         filtersObject[localize.DataScience.pdfFilter()] = ['pdf'];
         filtersObject[localize.DataScience.pngFilter()] = ['png'];
@@ -124,30 +126,47 @@ export class PlotViewer extends WebViewHost<IPlotViewerMapping> implements IPlot
             saveLabel: localize.DataScience.exportPlotTitle(),
             filters: filtersObject
         });
-        if (file) {
-            const ext = path.extname(file.fsPath);
-            switch (ext.toLowerCase()) {
-                case '.pdf':
-                    // tslint:disable-next-line: no-require-imports
-                    const SVGtoPDF = require('svg-to-pdfkit');
-                    const doc = new pdfkit();
-                    SVGtoPDF(doc, payload.svg, 0, 0);
-                    doc.pipe(this.fileSystem.createWriteStream(file.fsPath));
-                    doc.end();
-                    break;
-
-                case '.png':
-                    const buffer = new Buffer(payload.png.replace('data:image/png;base64', ''), 'base64');
-                    await this.fileSystem.writeFile(file.fsPath, buffer);
-                    break;
-
-                default:
-                case '.svg':
-                    // This is the easy one:
-                    await this.fileSystem.writeFile(file.fsPath, payload.svg);
-                    break;
+        try {
+            if (file) {
+                const ext = path.extname(file.fsPath);
+                switch (ext.toLowerCase()) {
+                    case '.pdf':
+                        traceInfo('Attempting pdf write...');
+                        // Import here since pdfkit is so huge.
+                        // tslint:disable-next-line: no-require-imports
+                        const SVGtoPDF = require('svg-to-pdfkit');
+                        const deferred = createDeferred<void>();
+                        // tslint:disable-next-line: no-require-imports
+                        const pdfkit = require('pdfkit');
+                        const doc = new pdfkit();
+                        const ws = this.fileSystem.createWriteStream(file.fsPath);
+                        traceInfo(`Writing pdf to ${file.fsPath}`);
+                        ws.on('finish', () => deferred.resolve);
+                        SVGtoPDF(doc, payload.svg, 0, 0);
+                        doc.pipe(ws);
+                        doc.end();
+                        traceInfo(`Finishing pdf to ${file.fsPath}`);
+                        await deferred.promise;
+                        traceInfo(`Completed pdf to ${file.fsPath}`);
+                        break;
+
+                    case '.png':
+                        const buffer = new Buffer(payload.png.replace('data:image/png;base64', ''), 'base64');
+                        await this.fileSystem.writeFile(file.fsPath, buffer);
+                        break;
+
+                    default:
+                    case '.svg':
+                        // This is the easy one:
+                        await this.fileSystem.writeFile(file.fsPath, payload.svg);
+                        break;
+                }
+
             }
 
+        } catch (e) {
+            traceError(e);
+            this.applicationShell.showErrorMessage(localize.DataScience.exportImageFailed().format(e));
         }
     }