Timeline

November

 * 9 November -- iOS 10.1.1 (14B150) released via IPSW's only.
 * 7 November -- iOS 10.2 beta 2, tvOS 10.1 beta 2 and watchOS 3.1.1 beta 2 released.

October

 * 31 October -- iOS 10.1.1, 10.2 beta, tvOS 10.1 beta and watchOS 3.1.1 beta released.
 * 24 October -- iOS 10.1, tvOS 10.0.1 and watchOS 3.1 released.
 * 20 October -- tvOS 10.0.1 beta 4 released.
 * 19 October -- iOS 10.1 beta 5 for iPhone 7 and iPhone 7 Plus released.
 * 17 October -- iOS 10.0.3 for iPhone 7 and iPhone 7 Plus and iOS 10.1 beta 4 released.
 * 12 October -- watchOS 3.1 beta 3 released.
 * 10 October -- iOS 10.1 beta 3 and tvOS 10.0.1 beta 3 released.
 * 4 October -- iOS 10.1 beta 2, tvOS 10.0.1 beta 2 and watchOS 3.1 beta 2 released.

September

 * 23 September -- iOS 10.0.2 released.
 * 21 September -- iOS 10.1 beta, tvOS 10.0.1 beta and watchOS 3.1 beta released.
 * 13 September -- iOS 10.0.1, tvOS 10.0 and watchOS 3.0 released.
 * 7 September -- iOS 10.0.1 GM, tvOS 10.0 GM and watchOS 3.0 GM released. Apple Watch Series 1, Apple Watch Series 2, iPhone 7, and iPhone 7 Plus announced.

August

 * 26 August -- iOS 10.0 beta 8 and tvOS 10.0 beta 7 released.
 * 25 August -- iOS 9.3.5 released.
 * 19 August -- iOS 10.0 beta 7 released.
 * 15 August -- iOS 10.0 beta 6, tvOS 10.0 beta 6 and watchOS 3.0 beta 6 released.
 * 9 August -- iOS 10.0 beta 5, tvOS 10.0 beta 5 and watchOS 3.0 beta 5 released.
 * 4 August -- iOS 9.3.4 released.
 * 1 August -- iOS 10.0 beta 4, tvOS 10.0 beta 4 and watchOS 3.0 beta 4 released.

July

 * 29 July -- Pangu9 for iOS 9.2-9.3.3 English version released.
 * 24 July -- Pangu9 for iOS 9.2-9.3.3 released.
 * 18 July -- iOS 10.0 beta 3, tvOS 10.0 beta 3 and watchOS 3.0 beta 3, iOS 9.3.3, watchOS 2.2.2 and tvOS 9.2.2 released.
 * 6 July -- iOS 9.3.3 beta 5 and tvOS 9.2.2 beta 5 released.
 * 5 July -- iOS 10.0 beta 2, tvOS 10.0 beta 2 and watchOS 3.0 beta 2 released.

June

 * 29 June -- iOS 9.3.3 beta 4 and tvOS 9.2.2 beta 4 released.
 * 21 June -- iOS 9.3.3 beta 3 and tvOS 9.2.2 beta 3 released.
 * 13 June -- iOS 10.0 beta, tvOS 10.0 beta and watchOS 3.0 beta released.
 * 6 June -- iOS 9.3.3 beta 2, tvOS 9.2.2 beta 2 and watchOS 2.2.2 beta released.
 * 2 June -- iOS 9.3.2 (13F72) is released for the iPad Pro (9.7 inch).

May

 * 23 May -- iOS 9.3.3 beta and tvOS 9.2.2 beta released.
 * 19 May -- iOS 9.3.2 is retracted for the iPad Pro (9.7 inch) due to a bug that may prevent usage, but continues to be signed.
 * 16 May -- iOS 9.3.2, tvOS 9.2.1 and watchOS 2.2.1 released.
 * 3 May -- iOS 9.3.2 beta 4 and tvOS 9.2.1 beta 4 released.

April

 * 27 April -- tvOS 9.2.1 beta 3 released.
 * 26 April -- iOS 9.3.2 beta 3 released.
 * 21 April -- tvOS 9.2.1 beta 2 re-released.
 * 20 April -- iOS 9.3.2 beta 2 and watchOS 2.2.1 beta 2 released. tvOS 9.2.1 beta 2 was also made available, but it was quickly retracted due to a mishap with publishing.
 * 6 April -- iOS 9.3.2 beta, watchOS 2.2.1 beta and tvOS 9.2.1 beta released.

March

 * 31 March -- iOS 9.3.1 released.
 * 28 March -- iOS 9.3 (13E237) released for iPad 2 (iPad2,1, iPad2,3, and iPad2,4), iPad 3, iPad 4, iPad Air, iPad mini, iPad mini 2, iPhone 4S, iPhone 5, iPhone 5c, iPhone 5s, iPod touch 5G.
 * 25 March -- iOS 9.3 (13E236) released for iPad 2 (iPad2,2).
 * 23 March -- Pangu released Apple TV 4G tvOS 9.0 - 9.0.1 jailbreak (v1.0.0).
 * 21 March -- iOS 9.3, tvOS 9.2 and watchOS 2.2 released to the public. iPad Pro (9.7 inch) and iPhone SE announced
 * 16 March -- Pangu9 1.3.1 (Windows)/1.1.1 (Mac) released to make untether of iOS 9.1 more stable.
 * 14 March -- iOS 9.3 beta 7 released.
 * 11 March -- Pangu9 1.3.0 (Windows)/1.1.0 (Mac) released to jailbreak 64-bit devices on iOS 9.1.
 * 10 March -- tvOS 9.2 beta 6 released.
 * 7 March -- iOS 9.3 beta 6 and watchOS 2.2 beta 6 released.
 * 1 March -- iOS 9.3 beta 5, tvOS 9.2 beta 5 and watchOS 2.2 beta 5 released.

February

 * 25 February -- Apple TV 3G software 7.2.1 released.
 * 22 February -- iOS 9.3 beta 4, tvOS 9.2 beta 4 and watchOS 2.2 beta 4 released.
 * 18 February -- iOS 9.2.1 (13D20) for iPhone 6, iPhone 6 Plus, iPhone 6s, iPhone 6s Plus, iPad mini 3, iPad mini 4, iPad Air 2, and iPad Pro (12.9 inch) released.
 * 8 February -- tvOS 9.2 beta 3, watchOS 2.2 beta 3 and iOS 9.3 beta 3 released.

January

 * 25 January -- tvOS 9.1.1, 9.2 beta 2, watchOS 2.2 beta 2 and iOS 9.3 beta 2 released.
 * 19 January -- iOS 9.2.1 released.
 * 14 January -- iOS 9.3 beta 1.1 released.
 * 11 January -- iOS 9.3, tvOS 9.1.1, tvOS 9.2 beta, and watchOS 2.2 beta released.
 * 4 January -- iOS 9.2.1 beta 2 released.

December

 * 25 December -- TaiG 2.4.5 released.
 * 16 December -- iOS 9.2.1 beta seeded to developers.
 * 8 December -- iOS 9.2, tvOS 9.1 and watchOS 2.1 released.

November

 * 30 November -- TaiG 2.4.4 released (no longer beta).
 * 20 November -- TaiG 2.4.4 beta released.
 * 18 November -- iOS 9.2 beta 4 and tvOS 9.1 beta 3 released.
 * 17 November -- iOS 9.1 (13B144) for iPad Pro (12.9 inch) released.
 * 11 November -- iPad Pro (12.9 inch) released.
 * 10 November -- iOS 9.2 beta 3 and tvOS 9.1 beta 2 released
 * 9 November -- tvOS 9.0.1 released.
 * 3 November -- iOS 9.2 beta 2 and tvOS 9.1 beta released.

October

 * 29 October -- iOS 9.2 public beta and tvOS 9.0 released.
 * 28 October -- Pangu9 1.0.0 for Mac released.
 * 27 October -- Pangu9 1.2.0 and iOS 9.2 beta released.
 * 22 October -- Seas0nPass 0.9.7 beta released to jailbreak Apple TV 2G running 6.2.1 tethered.
 * 21 October -- Pangu9 1.1.0, iOS 9.1, tvOS 9.0GM, watchOS 2.0.1 and iTunes 12.3.1 released.
 * 15 October -- Pangu9 1.0.1 released.
 * 14 October -- Pangu9 1.0.0 released to jailbreak iOS 9.0, 9.0.1 and 9.0.2.
 * 12 October -- iOS 9.1 beta 5 released.
 * 6 October -- iOS 9.1 beta 4 and tvOS 9.0 beta 3 released.

September

 * 30 September -- iOS 9.0.2 and 9.1 beta 3 released.
 * 24 September -- iOS 9.0.1 released for iPhone 6s and iPhone 6s Plus.
 * 23 September -- iOS 9.0.1 (excluding iPhone 6s and iPhone 6s Plus), 9.1 beta 2 and tvOS 9.0 beta 2 released.
 * 21 September -- watchOS 2.0 released to the public.
 * 16 September -- iOS 9.0 released to the public.
 * 9 September -- iOS 9.0GM, watchOS 2.0GM and iOS 9.1 beta released to developers. iPhone 6s, iPhone 6s Plus, iPad Pro (12.9 inch), iPad mini 4 and Apple TV 4G announced.

August

 * 13 August -- iOS 8.4.1 and iTunes 12.2.2 released.
 * 6 August -- iOS 9.0 beta 5 and watchOS 2.0 beta 5 released.
 * 4 August -- TaiG 1.1.0 for Mac released.
 * 2 August -- TaiG 1.0.0 for Mac released.

July

 * 30 July -- iOS 8.4.1 beta 2 released.
 * 21 July -- iOS 9.0 beta 4 and watchOS 2.0 beta 4 released.
 * 20 July -- TaiG 2.4.3 released, no longer a beta.
 * 16 July -- TaiG 2.4.3 beta released, optimises jailbreak process.
 * 15 July -- iPod touch 6G released.
 * 14 July -- iOS 8.4.1 beta released.
 * 13 July -- TaiG 2.4.2 Beta released, fixes 30% and 40% issues as well as bundling Cydia 1.1.23. PPJailbreak 2.0.0 released to jailbreak iOS 8.1.3 - 8.4 on Mac.
 * 11 July -- TaiG 2.4.1 released.
 * 10 July -- TaiG 2.4.1 Beta released, fixes 60% issue.
 * 7 July -- TaiG 2.3.1 released.
 * 6 July -- TaiG 2.3.1 Beta released, includes Cydia 1.1.20.
 * 3 July -- TaiG 2.3.0 released, which removes the setruid-patch
 * 2 July -- TaiG 2.2.1 released to address a security vulnarability allowing all apps to get root easily.

June

 * 30 June -- iOS 8.4 released. TaiG 2.2.0 released to jailbreak iOS 8.4.
 * 23 June -- TaiG 2.0.0 released to jailbreak iOS 8.1.3, 8.2 and 8.3.
 * 8 June -- Apple announces iOS 9, watchOS 2.0, and a release date of June 30 for iOS 8.4 at WWDC 2015.

May

 * 15 May -- geohot transfers ownership of The iPhone Wiki to saurik.

April

 * 23 April -- iOS 8.2 (build 12S506) released for Apple Watch.
 * 8 April -- iOS 8.3 and Apple TV 7.2 released.

March

 * 9 March -- iOS 8.2 released.

February

 * 23 February -- TaiG updated to version 1.3 to support iOS 8.2 beta and beta 2.
 * 12 February -- TaiG updated to version 1.2.1 to support iTunes 12.1.

January

 * 27 January -- iOS 8.1.3 and 7.0.3 (8.1.3) for Apple TV released.
 * 18 January -- PPJailbreak released to jailbreak iOS 8.0 - 8.1.2 on a Mac.

December

 * 9 December -- iOS 8.1.2 released.

November

 * 29 November -- TaiG released to jailbreak iOS 8.0 - 8.1.1 on all devices except Apple TV.
 * 18 November -- iOS 8.1.1 and Apple TV 7.0.2 released.

October

 * 22 October -- Pangu8 for iOS 8.x released.
 * 20 October -- iOS 8.1 released.
 * 16 October -- iPad Air 2 and iPad mini 3 announced.

September

 * 25 September -- iOS 8.0.2 released.
 * 24 September -- iOS 8.0.1 released. Critical bugs affecting Touch ID and cellular service was quickly discovered and the update was retracted.
 * 19 September -- Initial release of iPhone 6 and iPhone 6 Plus.
 * 17 September -- iOS 8.0 is released to the public, as well as 6.2.1 for the Apple TV 2G.
 * 9 September -- Apple announces the Apple Watch, iPhone 6, and iPhone 6 Plus.

June

 * 30 June -- iOS 7.1.2 and Apple TV 6.2 released to fix iBeacon connectivity, mail attachments not being encrypted and a bug with data transfers from third party accessories.
 * 29 June -- Pangu 1.1.0 released with lots of improvements.
 * 23 June -- Pangu released to jailbreak iOS 7.1.x untethered.
 * 1 June -- p0sixspwn updated to version 1.0.8 to support iOS 6.1.6 and fix iTunes 11.1+ crashes.

April

 * 22 April -- iOS 7.1.1 and Apple TV 6.1.1 released with bug fixes, including Touch ID fixes.

March

 * 27 March -- evasi0n7 updated to 1.0.8 to support iOS 7.0 (11A466) that shipped with some 5s and 5c iPhones
 * 10 March -- iOS 7.1, Apple TV iOS 6.1, iPad Air (iPad4,3) and iPad mini 2 (iPad4,6) released.
 * 1 March -- evasi0n7 updated to 1.0.7 to fix problem where bundled repository package information could not be refreshed/updated by Cydia and updated bundled Cydia package lists.

February

 * 26 February -- iTunes updated to 11.1.5 to fix crashing and improve iBooks compatibility on OS X.
 * 22 February -- evasi0n7 updated to version 1.0.6 to support iOS 7.0.6.
 * 21 February -- iOS 7.0.6 and iOS 6.1.6 released to address faulty SSL validation.
 * 5 February -- evasi0n7 updated to version 1.0.5 to support iOS 7.0.5.

January

 * 29 January -- iOS 7.0.5 released for iPhone 5c (iPhone5,4) and iPhone 5s (iPhone6,2), fixing network provisioning.
 * 22 January -- iTunes 11.1.4 released, adding Wish List and language improvements.
 * 12 January -- evad3rs releases evasi0n7 1.0.4 to fix important untether security bugs.
 * 11 January -- evad3rs releases evasi0n7 1.0.3 to fix iPad mini 2 bootloop issues, support iOS 7.1 beta 3 and include Cydia 1.1.9.

December

 * 31 December -- evad3rs releases evasi0n7 1.0.2 to fix iPad 2 bootloop issues.
 * 30 December -- iH8sn0w, SquiffyPwn, and winocm release p0sixspwn, an untethered jailbreak for iOS 6.1.3 through 6.1.5, for Mac OS X.
 * 24 December -- evad3rs releases evasi0n7 1.0.1 to completely remove Chinese piracy store.
 * 22 December -- evad3rs releases evasi0n7, an untethered jailbreak for iOS 7.0 through 7.0.4.

November

 * 14 November -- iOS 7.0.4, 6.1.5 for iPod touch 4G to fix FaceTime bugs and Apple TV 6.0.2 released.
 * 1 November -- iPad Air released.

October

 * 24 October -- Apple TV firmware updated to 6.0.1.
 * 22 October -- iOS 7.0.3 released to fix various bugs including a passcode bug. iPad Air and iPad mini 2 announced.

September

 * 26 September -- iOS 7.0.2 released to address Lock screen issues.
 * 23 September -- Apple releases a patched version of the Apple TV 6.0 update.
 * 20 September -- Initial release of iPhone 5c and iPhone 5s. iOS 7.0.1 is also made available for these devices. A 6.0 update for the Apple TV was also released, but is pulled due to problems.
 * 18 September -- iOS 7.0 released for the iPad 2 and newer, iPad mini, iPhone 4 and newer, iPod touch 5G.
 * 10 September -- Apple announces the iPhone 5c and iPhone 5s.

June

 * 25 June -- iFaith 1.5.9 released.
 * 19 June -- Apple TV firmware 5.3 released.
 * 10 June -- Apple unveils a completely-revamped iOS 7 at WWDC.

May

 * 30 May -- Apple quietly unveils a 16 GB version of the iPod touch 5G that omits the rear camera, replacing the iPod touch 4G.
 * 2 May -- iOS 6.1.4 released for iPhone 5.

April

 * 13 April -- iFaith updated to version 1.5.8.
 * 11 April -- Sn0wbreeze updated to version 2.9.14.
 * 10 April -- iFaith updated to version 1.5.7.

March

 * 10 March -- iFaith updated to version 1.5.6.
 * 19 March -- Apple releases iOS 6.1.3 to patch multiple security-related bugs and improve Maps for Japanese users.
 * 12 March -- evad3rs updated evasi0n to 1.5.3.
 * 11 March -- evad3rs updated evasi0n to 1.5.2.
 * 10 March -- iFaith updated to version 1.5.5.
 * 5 March -- evad3rs updated evasi0n to 1.5.1.

February

 * 23 February -- iFaith updated to version 1.5.4.
 * 23 February -- evad3rs updated evasi0n to 1.5. iFaith updated to version 1.5.3.
 * 19 February -- Apple releases iOS 6.1.2 as a hotfix to address Exchange issues. Evasi0n was updated to support iOS 6.1.2 later the same day.
 * 13 February -- Seas0nPass updated to support iOS 5.2 for the Apple TV 2G untethered jailbreak.
 * 11 February -- Apple releases iOS 6.1.1 for the iPhone 4S as a hotfix to address connectivity issues. evasi0n was updated to support iOS 6.1.1 later the same day.
 * 4 February -- The evad3rs release evasi0n to jailbreak iOS 6.x.

January

 * 28 January -- Apple releases iOS 6.1.

December

 * 18 December -- Apple releases iOS 6.0.2 containing bug fixes for the iPhone 5 and iPad mini.

November

 * 30 November -- Apple releases iTunes 11.
 * 12 November -- sn0wbreeze is updated to version 2.9.7.
 * 2 November -- Inital release of iPad 4 and iPad mini in first set of countries.
 * 1 November -- Apple releases iOS 6.0.1.

October

 * 23 October -- Apple announces new iPad 4 and iPad mini.
 * 14 October -- The iPhone Dev Team releases redsn0w 0.9.15b1, which lets A5(X) users with the appropriate SHSH blobs remain on, or update to, iOS 5.x.

September

 * 21 September -- Initial release of iPhone 5 in first set of countries.
 * 19 September -- Apple releases iOS 6.
 * 12 September -- Apple announces new iPhone 5 and release date of iOS 6.

June

 * 18 June -- iPhone Dev Team releases a new version of redsn0w (0.9.14b1), adding the capability to downgrade iPhone 3G/3GS Baseband from the 06.15.00 iPad baseband to the latest unlockable iPhone baseband (05.13.04). This allows 3G/3GS users that had upgraded to the iPad baseband, thus losing the GPS function and the ability to restore to stock firmware, to get back to an iPhone baseband, making their devices behave as intended again, as well as being unlockable by ultrasn0w.
 * 14 June -- iPhone Dev Team releases a developer version of redsn0w (0.9.13dev1), which jailbreaks limera1n susceptible devices running iOS 6.0 beta. This version doesn't hacktivate nor install Cydia, as it hasn't been ported to iOS 6 just yet. This jailbreak, however, installs afc2 and SSH, enabling developers to fix and prepare their apps to the next iOS version.
 * 11 June -- Apple announces iOS 6 at WWDC 2012, and seeds the first beta to developers.

May

 * 25 May -- The Chronic Dev Team releases Absinthe 2.0, providing an untethered jailbreak for all devices except the Apple TVs and iPad 2 (iPad2,4). (Seas0nPass was also updated to include Absinthe's untether for the Apple TV 2G.)
 * 7 May -- Apple releases iOS 5.1.1.

March

 * 7 March -- Apple releases iOS 5.1 and announces new devices: iPad 3, Apple TV 3G, and the iPad 2 (iPad2,4).

January

 * 20 January -- Absinthe was released to jailbreak and untether the A5 devices running iOS 5.0 and 5.0.1.
 * 18 January -- Apple announces iBooks version 2.0.

December

 * 30 December -- pod2g's untether for iOS 4.4.4 makes its way into a new version of Seas0nPass for Apple TV 2G owners.
 * 27 December -- pod2g's untether for iOS 5.0.1 is released in new versions of PwnageTool and redsn0w, and as a Cydia package called Corona (by the Chronic Dev Team) for devices already jailbroken on 5.0.1.
 * 15 December -- Apple releases iOS 4.4.4 for the Apple TV 2G, as well as a minor update (5.0.1 build 9A406) for the iPhone 4S to address SIM card issues.
 * 4 December -- iFaith 1.4 is released, which can circumvent the APTicket nonce on devices vulnerable to limera1n's exploit.

November

 * 10 November -- iOS 5.0.1 is released in an attempt to fix battery-related issues. It's the first non-beta available as an OTA update.

October

 * 14 October -- The iPhone 4S is officially released, although some preorders were delivered early.
 * 12 October -- iOS 5.0 is released. The iPhone 4S IPSW came with 04.11.08 due to a goof on Apple's side.
 * 5 October -- Steve Jobs passes away.
 * 4 October -- Apple announces the new iPhone 4S.

September

 * 19 September -- redsn0w 0.9.9 beta 1 is released, introducing a new UI and many features (like submitting SHSHs to the Cydia Server.
 * 17 September -- MyGreatFest, first iCommunity and jailbreak centered convention was held.

July

 * 15 July -- Apple releases iOS 4.2.9 and 4.3.4, patching all jailbreaking-related vulnerabilities (aside from those in the bootrom).
 * 6 July -- comex releases Saffron, the first public jailbreak for the iPad 2.
 * 2 July -- A beta version of the upcoming jailbreak from comex for the iPad 2, making use of a PDF exploit, was leaked. A hotfix by Apple is expected very soon.

June

 * 1 June -- iH8sn0w releases iFaith to dump SHSH blobs from a device.

May

 * 6 May -- PwnageTool, redsn0w, and sn0wbreeze are updated for iOS 4.3.3 support (and in the case of sn0wbreeze, iOS 4.2.8 support as well).
 * 3 May -- Apple releases iOS 4.2.8 and 4.3.3 to address the location-tracking controversy. Once more, current untethering vulnerabilities remained unpatched.

April

 * 24 April -- PwnageTool, redsn0w, and sn0wbreeze are updated for iOS 4.3.2 support (and in the case of sn0wbreeze, iOS 4.2.7 support as well).
 * 14 April -- Apple releases iOS 4.2.7 and 4.3.2 to fix security issues and connection issues for iPad 2 (iPad2,3), but leaves untethering vulnerabilities unpatched.
 * 3 April -- All major jailbreak tools (redsn0w, PwnageTool, sn0wbreeze) get updated to includes i0n1c's untether code to jailbreak devices compatible with iOS 4.3.1 except the iPad 2.

March

 * 25 March -- Apple releases iOS 4.3.1, properly blocking comex's exploit.
 * 13 March -- comex shows a remotely jailbroken iPad 2 (iPad2,3).
 * 11 March -- Release of the iPad 2 in the USA. The exploits for limera1n (geohot), SHAtter (p0sixninja), and comex's kernel exploit were closed by Apple.
 * 9 March -- Apple releases iOS 4.3, fixing the HFS Legacy Volume Name Stack Buffer Overflow vulnerability.

February

 * 15 February -- New version of both PwnageTool and sn0wbreeze were released to support 4.2.1 and untethered using the feedface exploit.
 * 7 February -- The Chronic Dev Team release a version of greenpois0n to jailbreak the iPhone 4 (iPhone3,3), using the HFS Legacy Volume Name Stack Buffer Overflow.
 * 3 February -- Jaywalker of the Chronic Dev Team posts a video of custom boot using a soon to be released version of greenpois0n.

January

 * 12 January -- Apple discontinues iOS support for iPhone 3G and iPod touch 2G since today's beta release of iOS 4.3. Also first time a beta iOS for Apple TV 2G is released.
 * 11 January -- Verizon announces iPhone 4 (iPhone3,3).

November

 * 28 November -- ultrasn0w 1.2 is released by the iPhone Dev Team to unlock iPhone 3G and iPhone 3GS on baseband 6.15.00
 * 22 November -- Apple releases iOS 4.2.1 (respectively 4.2 for Apple TV 2G)

October

 * 31 October -- The Dev Team releases redsn0w 0.9.6b2 which jailbreaks iOS 4.1, 4.2 and 3.2.2 on every device available at the time of release (except for iPT 2G MC). It also includes "DFU" button allowing to flash custom IPSW from Windows (see blog post).
 * 20 October -- The Dev Team releases PwnageTool 4.1 which jailbreaks iOS 4.1 and 3.2.2 on every device available at the time of release. (see blog post)
 * 18 October -- Chronic Dev Team releases greenpois0n RC4 which added support for iPod touch 2G (MC and MB) for an untethered jailbreak using comex's kernel exploit and the usb_control_msg(0xA1, 1) Exploit.
 * 12 October -- Chronic Dev Team releases greenpois0n after switching its exploit from SHAtter to limera1n, in the hope that SHAtter remains for 5th generation devices. (The exploit limera1n uses was fixed in the iBoot revision found in iOS 4.2 beta 2, which means Apple knows about the vulnerability and the next bootrom revision may have it patched.)
 * 10 October -- Following the first limera1n beta release, geohot released multiple versions, each fixing bugs affecting previous releases. Chronic Dev Team officialy anounces that, in order to keep SHAtter undisclosed and possibly preserve it for 5th generation devices, greenpois0n would be delayed in order to incorporate this new exploit limera1n uses.
 * 9 October -- In order to push Chronic Dev Team to change the exploit used on greenpois0n, geohot rushed out a beta version of limera1n.
 * 8 October -- Geohot comes back to the scene with a new bootrom exploit believed to work on all devices, as shown on the resurrected limera1n web site. He prompts Chronic Dev Team to use his exploit instead of SHAtter, but, since greenpois0n is already scheduled to October 10, it may be not possible. Geohot ETA'd his limera1n release to October 11, if greenpois0n can't be changed to use this new exploit. This decision, however, would burn 2 bootrom exploits: SHAtter itself and the one used by limera1n, which is unpatchable by firmware updates.
 * 6 October -- Chronic Dev Team issues expected ETA of greenpois0n as October 10, featuring the new SHAtter exploit for devices with the S5L8930.

September

 * 30 September -- MuscleNerd of the iPhone Dev Team posts the first video of an Apple TV 2G jailbroken via SHAtter.
 * 27 September -- MuscleNerd of the iPhone Dev Team posts the first video of an iPod touch 4G jailbroken via SHAtter.
 * 20 September -- pod2g discloses details about the usb_control_msg(0xA1, 1) Exploit‎ here at The iPhone Wiki. It was used in redsn0w the following day.
 * 9 September -- The existence of SHAtter is revealed. Further details were not released, however.
 * 8 September -- Apple releases the iPod touch 4G, and iOS 4.1, closing the AT+XAPP Vulnerability.
 * 1 September -- Apple event. They announced the new iPod touch 4G, Apple TV 2G, iOS 4.1, and iTunes 10.

August

 * 12 August -- Saurik releases the first version of PDF Patcher, which installs Apple's patch for the FreeType vulnerability (used in conjunction with other exploits by Star). It works on firmwares as far back as 2.x, and renders iOS 3.2.2 and 4.0.2 useless for jailbreakers. Jailbreaking and installing this patch is currently the only way for users of first generation iPod touches and iPhones to protect themselves against malicious use of the exploit.
 * 11 August -- Apple releases iOS 4.0.2 for iPhone/iPod touch and iPhone OS 3.2.2 for iPad as a hotfix for Star's exploits. Ultrasn0w's exploit remains, since there's no baseband update on those versions.
 * 3 August -- Just before midnight in planetbeing's timezone ultrasn0w has been released by the iPhone Dev Team to unlock the iPhone 4.
 * 1 August -- comex releases Star, a jailbreak for all iDevices with iPhone OS 3.1.2 through iOS 4.0.1.

July

 * 30 July -- iPhone 4 is released in major countries (second wave).
 * 26 July -- Jailbreaking is now officially legal in the U.S.A.: EFF Wins New Legal Protections for Cell Phone Jailbreakers and Unlockers
 * 15 July -- Apple releases iPhone OS 3.2.1 and iOS 4.0.1.

June

 * 24 June -- iPhone 4 is launched.
 * 22 June -- iPhone Dev Team releases PwnageTool 4.0 and later 4.0.1 for all devices on 4.0 except those with newer bootroms (some iPod touch 2G and iPhone 3GS devices, and all iPod touch 3G and newer devices).
 * 21 June -- iPhone Dev Team releases redsn0w 0.9.5 to jailbreak 4.0 on iPhone 3G and iPhone touch 2G (old bootrom), iPhone Dev Team releases ultrasn0w 0.93, an unlock for baseband firmwares 04.26.08, 05.11.07, 05.12.01, and 05.13.04 and Apple releases iOS 4.0
 * 19 June -- geohot holds a speech at the Nuit du Hack

May

 * 3 May -- Windows version of Spirit has been updated to not require Windows 98 compatibility mode to run and fixed a photo deletion issue.
 * 2 May -- comex releases Spirit, an untethered jailbreak for all iDevices with iPhone OS 3.1.2 through 3.2.

April

 * 3 April -- Apple releases the iPad.

February

 * 12 February -- sherif_hashim discovers AT+XAPP Vulnerability and passes it to MuscleNerd, an elite member of the iPhone Dev Team
 * 2 February -- Apple releases iPhone OS 3.1.3, closing usb_control_msg(0x21, 2) vulnerability used by blackra1n, redsn0w, et. al.

November

 * 3 November -- geohot releases blackra1n RC3, a software jailbreak for all devices. Includes a new unlock for baseband 05.11.07 called blacksn0w and is also noticeably faster than previous versions.

October

 * 11 October -- geohot releases blackra1n RC1, a 30 second software jailbreak for all devices, including a tethered jailbreak for the iPod touch 3G, and iPhone 3GS and iPod touch 2G units with newer bootrom revisions.

September

 * 24 September -- iH8sn0w discovers the AT+XEMN crash independently.
 * 9 September -- The iPod touch 3G with S5L8922 processor is released. iPod touch 2G and iPhone 3GS units continue shipping, but with a new bootrom (240.5.1 and 359.3.2 respectively) that is no longer vulnerable to the 0x24000 Segment Overflow.
 * 9 September -- Apple releases iPhone OS 3.1 (7C144) for iPhones and 3.1.1 (7C145) for iPod touches, closing the iBoot Environment Variable Overflow and AT+XLOG + AT+FNS Baseband Exploits.

July

 * 14 July -- geohot releases purplesn0w, a software unlock for the X-Gold 608 using the same exploit as ultrasn0w, but handled differently. Minutes later, an explanation and source code was posted.
 * 7 July -- The iPhone Dev Team updates redsn0w and ultrasn0w to version 0.8, now with iPhone 3GS support. Saurik also updates WinterBoard to support the iPhone 3GS.
 * 3 July -- geohot releases purplera1n, a software jailbreak for the iPhone 3GS.

June

 * 28 June -- geohot posts pictures on his blog of the first fully jailbroken iPhone 3GS.
 * 25 June -- It's discovered that iPhone 3GS is vulnerable to the 0x24000 Segment Overflow.
 * 24 June -- The iPhone Dev Team releases ultrasn0w, an unlock for X-Gold 608 thanks to a new exploit discovered by Oranav.
 * 23 June -- geohot announces he's found a new exploit in iBoot he calls purplera1n.
 * 19 June -- Release of iPhone 3GS to the public and the release of PwnageTool 3.0 and redsn0w for jailbreaking devices running iPhone OS 3.0
 * 17 June -- Apple releases iPhone OS 3.0.
 * 8 June -- Apple announces the iPhone 3GS.

March

 * 10 March -- Information about the 0x24000 Segment Overflow exploit used for the iPod touch 2G untethered jailbreak is released thanks to the combined work of chronic, CPICH, posixninja, pod2g, ius, planetbeing, MuscleNerd, and co. after being leaked and sold by NitroKey. To prevent users wasting their money on a stolen exploit, the Hybrid DevTeam decided to release it immediately.

January

 * 31 January -- The iPhone Dev Team released redsn0w Lite, a tethered iPod touch 2G jailbreak. It combines the ARM7 Go vulnerability with the well-established pwnage flow for other Apple mobile devices. It was bundled in a way that allowed usage on iPhone OS 2.2.1 by uploading iBoot from iPhone OS 2.1.1, which is vulnerable to ARM7 Go, to the device while in DFU Mode.
 * 29 January -- Apple releases iPhone OS 2.2.1, closing the AT+stkprof exploit.
 * 25 January -- 0wnboot is released to chronicdev google code page, thanks to AriX, chronic, CPICH, westbaer, ius, pod2g, the rest of the iPod devel crew on IRC, and to the #iphone-hax lab rats. Within days, AriX and the Chronic Dev Team got a ramdisk booting for a tethered jailbreak.
 * 17 January -- MuscleNerd of the iPhone Dev Team shows a video demo of the first jailbroken iPod touch 2G.
 * 16 January -- ARM7 Go vulnerability disclosed where else but here on The iPhone Wiki, for developers to poke and prod at.
 * 15 January -- The iPhone Dev Team tweets the VFDecrypt key for iPhone OS 2.2 on iPod touch 2G, demonstrating for the first time that unsigned code can now be run on that device.
 * 1 January -- The iPhone Dev Team releases yellowsn0w 0.9 beta for baseband 02.28.00.

December

 * 27 December -- 25C3 presentation "Hacking the iPhone"
 * 21 December -- MuscleNerd, of the iPhone Dev Team does a live demo of the 3G unlock, dubbed as yellowsn0w: http://qik.com/video/729275

November

 * 21 November -- Apple releases iPhone OS 2.2.

September

 * 9 September -- Apple releases iPhone OS 2.1. iPod touch 2G, which no longer had the Pwnage 2.0 exploit, is revealed.

August

 * 18 August -- Apple releases iPhone OS 2.0.2. iPhone Dev Team releases QuickPwn, a 2.x pwnage/ramdisk combination exploit that allows jailbreaking without needing to create custom IPSWs.
 * 4 August -- Apple releases iPhone OS 2.0.1.

July

 * 22 July -- TA_Mobile hardware dumps the 3G baseband (bootloader 5.8 & FW 1.45.00) by desoldering the NOR.
 * 19 July -- iPhone Dev Team releases PwnageTool 2.0, jailbreaking and unlocking the 2.0 software on the iPhone (1st generation) and jailbreaking iPhone OS 2.0 on the iPhone 3G and iPod touch (1st generation).
 * 15 July -- Apple releases iPhone OS 1.1.5 for the iPod touch (1st generation).
 * 11 July -- iPhone 3G is released. Apple also releases iPhone OS 2.0 and MobileMe on the same date, resulting in server issues.

June

 * 9 June - iPhone 3G is announced at WWDC '08.

April

 * 3 April -- iPhone Dev Team releases PwnageTool 1.0, making use of the pmdx exploit (to patch RSA checks out of the kernel, to write unsigned to NOR)

March

 * 12 March -- iPhone Dev Team releases dual-boot jailbreak method, only to be silently fixed in 2.0.
 * 4 March -- George Zhu (n000b) releases iLiberty / iLiberty+.

February

 * 28 February -- Cydia is released as an open-source alternative to Installer.app, and prepares to take over the jailbreak application scene upon 2.0's release.
 * 26 February -- Apple releases iPhone OS 1.1.4.
 * 11 February -- Zibri leaks the Ramdisk Hack in ZiPhone, the first all-in-one unlock, activate, jailbreak solution.
 * 8 February -- geohot releases software unlock for 4.6. Apple states 25% of phones were never activated with AT&T.

January

 * 28 January -- iPhone Dev Team releases Soft Upgrade jailbreak for 1.1.3.
 * 24 January -- Nate True releases a version of iBrickr that used the Soft Upgrade method to jailbreak 1.1.3.
 * 18 January -- Geohot and his friends unlocked 1.1.2 OTB 4.6 by test point, the unbeatable version at that time.
 * 18 January -- iPhone Dev Team posts YouTube video of a jailbroken 1.1.3, which was made possible by the dual boot jailbreak from bgm.
 * 15 January -- Apple releases iPhone OS 1.1.3, closing the mknod exploit. In addition, everything now runs as "mobile" instead of "root."

November

 * 15 November -- Baseband bootloader 4.6 is found on new iPhone devices, which initially had no unlock.
 * 12 November -- Apple releases iPhone OS 1.1.2, closing the LibTiff and Symlinks exploits.
 * 2 November -- AppSnapp is released, bringing jailbreaking to the mainstream iPhone user.

October

 * 23 October -- iPhone-Elite Team releases the Virginizer.
 * 14 October -- AriX releases iJailBreak, the first automated iPod touch jailbreak for the Mac.
 * 12 October -- planetbeing releases touchFree, the first automated iPod touch jailbreak.
 * 10 October -- cmw (aka Niacin) and Dre release the LibTiff exploit to jailbreak the iPod touch, which is later adapted for use in AppSnapp.

September

 * 27 September -- Apple releases iPhone OS 1.1.1.
 * 11 September -- iPhone Dev Team releases iUnlock, first free software unlock.
 * 10 September -- IPSF releases first paid software unlock.
 * 9 September -- Apple announces the iPod touch at a media event.

August

 * 23 August -- geohot and team release hardware unlock method.
 * 21 August -- Installer.app is released by Nullriver, first GUI apps are distributed.

July

 * 23 July -- First phones are used with other carriers by means of SIM hacks.
 * 20 July -- nightwatch adapts a toolchain to the iPhone. The first apps are compiled.
 * 9 July -- iPhone Dev Team releases a jailbreak method. The first use of this is ringtones.
 * 3 July -- DVD Jon first cracks activation. People can use the apps on the phone without a subscription.

June

 * 29 June -- iPhone is released. World's most hyped consumer product.
 * 26 June -- The iPhone Dev Team was formed.