In 1988, a Dungeon Master preparing an Advanced Dungeons & Dragons campaign could surround himself with rulebooks, handwritten notes, graph paper, dice, encounter tables, monster statistics, treasure charts, and enough loose paper to cover a dining room table. Strategic Simulations, Inc. believed a home computer could help with some of that work.
The result was Dungeon Masters Assistant, Volume I: Encounters, an unusual official AD&D computer product that arrived during the first great wave of licensed Dungeons & Dragons software. Unlike Pool of Radiance, Heroes of the Lance, and the other computer adventures appearing under SSI’s new agreement with TSR, Dungeon Masters Assistant was not intended to take players into a digital dungeon.
Its own documentation made the distinction explicit: “This is not a game.”
Instead, SSI attempted to place the computer beside the tabletop Dungeon Master. The machine could search monster records, generate encounters, roll dice, organize information, and prepare material that would later be used in a conventional AD&D session. A second volume, Characters & Treasures, expanded the idea in 1989 by automating character creation and the enormous assortment of treasure tables found across the game’s rulebooks.
The two programs occupied a curious place between tabletop role-playing and computer gaming. They were software products built around a game, but they were not computer games in the conventional sense. Their purpose was to make another game easier to prepare and run. In that way, Dungeon Masters Assistant became an early experiment in something that would become increasingly familiar decades later: using digital tools to support a role-playing campaign that still existed primarily around a table.
SSI Wins the Advanced Dungeons & Dragons License
The story of Dungeon Masters Assistant begins with one of the most important licensing agreements in early computer role-playing history.
In 1987, TSR opened the computer rights to Advanced Dungeons & Dragons to outside competition. SSI was already well established as a publisher of computer wargames and fantasy titles, but the AD&D license promised access to one of the most recognizable names in tabletop gaming.
Competition was substantial. Hartley and Patricia Lesser reported in the November 1987 issue of Dragon that ten companies competed for the rights. SSI president Joel Billings told the magazine that his company had approached TSR about computer licensing more than a year earlier, only to find that TSR was not ready at that time. When the opportunity finally opened in 1987, SSI made its case directly.
Billings recalled taking six computers to TSR and demonstrating several fantasy games the company had already produced. SSI’s argument was not simply that it could program a role-playing game. Billings emphasized that members of the company’s development staff actually knew AD&D, played it, and wanted to treat the property seriously.
The presentation was important enough that the original packet prepared by SSI survives in the Joel Billings Strategic Simulations papers at The Strong National Museum of Play. The archive identifies a “SSI presentation to TSR for Dungeons & Dragons license” from spring 1987 in Box 1, Folder 5. The licensing agreement itself was signed in May.
SSI did not plan to use the license for a single kind of product.
In its Summer 1987 Inside SSI newsletter, the company described three major lines under development. One would consist of computer role-playing games in which the computer acted as Dungeon Master. Another would focus on action-oriented software. The third would be a series of Dungeon Master’s Assistant programs capable of generating encounters, non-player characters, treasure, and other material.
That distinction was present before Pool of Radiance or Dungeon Masters Assistant reached store shelves. SSI was already thinking beyond the idea of merely converting AD&D into a computer role-playing game. It also wanted to use the computer as a tool for people who intended to keep playing AD&D with books, dice, and a human Dungeon Master.
Turning the Computer Into a Dungeon Master’s Tool
The concept became clearer as SSI’s AD&D projects moved toward release.
By the winter of 1987, Inside SSI described the first Dungeon Master’s Assistant as a monster database and encounter generator planned for late summer 1988. Around the same time, SSI representatives explained the broader philosophy to Dragon. Rather than asking the computer to replace the Dungeon Master, the utility project was intended to handle some of the bookkeeping associated with AD&D so that the human Dungeon Master could spend more time on the creative side of the campaign.
That difference mattered.
Running AD&D in the 1980s could require substantial preparation. A Dungeon Master might need to determine what creatures inhabited an area, consult encounter tables, check monster statistics, calculate treasure, record weapons and armor, prepare spell information, and keep everything organized for use during play. The more elaborate the campaign became, the more information the Dungeon Master could find himself managing.
SSI saw the personal computer as a way to reduce that administrative burden without removing the person who actually created and controlled the adventure.
The first volume concentrated on encounters. Later volumes were expected to tackle other portions of the Dungeon Master’s workload. The concept was therefore not a computer adaptation of an AD&D campaign. It was closer to an electronic reference desk sitting beside one.
Volume I: Encounters
Dungeon Masters Assistant, Volume I: Encounters appeared in 1988 as an official Advanced Dungeons & Dragons computer product from SSI and TSR.
The credits associated with the program identify Paul Murray, Victor Penman, and longtime TSR designer James M. Ward. SSI’s Fall 1988/Winter 1989 catalog advertised Apple II and Commodore 64/128 editions as available, with an IBM version scheduled for December. A later SSI catalog listed Apple II, Commodore 64/128, and IBM editions as available.
The numbers were a major part of SSI’s sales pitch.
According to the original manual and SSI catalog, the program contained more than 1,000 encounters and more than 1,300 monsters and characters. Its database incorporated the creatures from the official AD&D Monster Manual and Monster Manual II, placing a large portion of the game’s monster information inside a searchable computer utility.
That database was only the starting point.
The Dungeon Master could generate an encounter for a particular monster or allow the program to select encounters according to location. The manual described categories based on the environment in which the adventurers were traveling, allowing the software to produce encounters appropriate to different wilderness or dungeon conditions.
A generated encounter did not have to remain exactly as the computer created it. Users could edit results, create original encounters, add monsters, and modify portions of the database and encounter tables. The manual devoted substantial space to monster editing, encounter editing, treasure information, and the construction of more complicated encounter records.
The program could also produce the information before a session and save it to disk or send it to a printer. This was an important part of the intended workflow. The Dungeon Master did not necessarily need a computer running beside the players throughout the night. The computer could be used as a preparation machine, generating material that would later become part of the paper campaign.
Preparing the Adventure Before the Players Arrived
The original manual is especially revealing because SSI openly acknowledged the limitations of using the program during an active game.
It explained that encounters could be generated during play, but warned that doing so might delay the session while the computer completed the process. Preparing encounters in advance, printing them, or saving them for later retrieval could make more sense.
That admission captures the reality of late-1980s home computing.
Modern players accustomed to instant databases, online character sheets, virtual tabletops, and searchable rule systems can easily underestimate how different the experience was on an Apple II, Commodore 64, or early IBM-compatible computer. Programs were loaded from floppy disks. Data might need to be swapped between disks. Storage was limited. Printers were useful but not universal. Even navigating a large database could interrupt the rhythm of a tabletop session.
The program therefore worked best when viewed not as an electronic referee constantly running the game, but as another tool in the Dungeon Master’s preparation process.
SSI’s catalog promised that the program could reduce preparation by several hours per session. Whether it actually accomplished that goal depended heavily on the computer, the Dungeon Master, and how the program was used. Contemporary reviewers would soon disagree sharply on the answer.
Praise and Frustration in the Contemporary Reviews
Early coverage could be enthusiastic.
In September 1988, Computer Entertainer described Dungeon Masters Assistant as the first AD&D utility program produced through the SSI and TSR relationship. The magazine discussed its database of more than 1,000 encounters and 1,300 monsters and characters, along with its ability to modify data, store results, and assist with the bookkeeping surrounding treasure, spells, experience, armor, and weapons.
The review recommended the program and argued that players of traditional AD&D could reach the actual game more quickly by allowing the computer to handle some of the preparation.
The following spring, RUN offered a much harsher assessment of the Commodore 64 edition.
Reviewer John Ryan gave Dungeon Masters Assistant a C-minus. He accepted the basic idea that AD&D could benefit from a computer utility, but found the implementation cumbersome. Generating encounters required navigating several menus and, on the Commodore version, swapping disks. He considered the database and editing tools primitive and concluded that the program was not particularly convenient for interactive use while an AD&D session was already underway.
Ryan did acknowledge the use that SSI’s own manual had effectively suggested: campaign preparation before the players arrived.
The disagreement between the two reviews tells much of the story. The concept of a digital Dungeon Master’s assistant was attractive. The challenge was making that concept fast and convenient on the home computers of 1988.
Volume II: Characters & Treasures
SSI returned to the idea in 1989 with Dungeon Masters Assistant, Volume II: Characters & Treasures.
Where the first program concentrated on encounters and monsters, the second moved toward two other time-consuming parts of AD&D: creating characters and generating treasure.
The SSI catalog credited Al Escudero, James M. Ward, and David Wong. Once again the company emphasized that this was a utility rather than a stand-alone adventure. The manual stated that players needed the AD&D paper materials to take advantage of the program and described the software as something intended to enhance TSR’s tabletop products rather than replace them.
Character generation was considerably more complicated than simply producing six ability scores.
Characters & Treasures could create player characters and non-player characters using the classes found in the Players Handbook. Multi-class characters were supported, and users who activated the Unearthed Arcana material could also generate Cavaliers and Barbarians. The program accounted for elements such as class and racial abilities, languages, spells, and other information needed for a usable AD&D character.
Once created, characters could be edited, saved to disk, or printed.
For a Dungeon Master trying to populate a settlement with several inhabitants, create a group of hirelings, or produce an unexpected NPC during campaign preparation, the appeal was easy to understand. Instead of manually repeating the character creation process, the computer could perform much of the underlying work and present the result in a form ready for further customization.
Gems, Jewelry, Magic Items, and Intelligent Weapons
The second half of Volume II addressed one of AD&D’s other great collections of tables: treasure.
The program could generate gems and jewelry, including their characteristics, produce standard treasure types associated with encounters, and create magical items. SSI advertised support for the magic-item material in the Dungeon Masters Guide and Unearthed Arcana, along with treasure information tied to the Monster Manual and Monster Manual II.
The catalog specifically promoted the program’s usefulness for generating large numbers of gems, pieces of jewelry, and intelligent weapons, all tasks that could involve repeated die rolls and table consultation when performed manually.
Volume II also included a configurable dice roller. The user could enter ordinary expressions for multiple dice and modifiers, or instruct the computer to perform repeated sets of rolls and record the individual results.
In isolation, a computerized dice roller was a small feature. Taken together with the character and treasure generators, however, it illustrated SSI’s larger approach. The company was identifying repetitive pieces of tabletop administration and asking which of them could be handed to the computer while the Dungeon Master retained control of the campaign itself.
From Apple II and Commodore to Amiga and MS-DOS
The second volume also demonstrates the changing computer market at the end of the 1980s.
SSI promoted Characters & Treasures for several systems, and the original materials show the program moving across the Apple II, Commodore 64/128, IBM-compatible, and Amiga markets. Computer Entertainer reported in December 1989 that Commodore 64/128 and Apple II versions had appeared earlier, while Amiga and MS-DOS editions had subsequently been released.
All versions carried a suggested retail price of $29.95 according to that report.
The cross-platform strategy placed the utility beside SSI’s much more recognizable AD&D games. The company’s 1989-1990 catalog grouped both volumes beneath the heading “AD&D Game Utilities,” while pages around them advertised products such as War of the Lance, Curse of the Azure Bonds, and Dragons of Flame.
The physical and marketing context is important. SSI was not treating Dungeon Masters Assistant as an unrelated productivity program. It belonged to the same licensed AD&D family as the company’s fantasy adventures and wargames, even though its purpose was fundamentally different.
The Other Side of SSI’s AD&D Computer Line
Today, SSI’s relationship with Advanced Dungeons & Dragons is remembered primarily through its games.
Pool of Radiance launched the famous Gold Box line and helped establish a model for translating AD&D rules into a computer role-playing system. Curse of the Azure Bonds, Secret of the Silver Blades, Champions of Krynn, and the later Eye of the Beholder games expanded SSI’s place in computer RPG history.
Dungeon Masters Assistant represents another side of the same licensing agreement.
SSI’s earliest plans did not assume that computers would make tabletop AD&D obsolete. The company envisioned computer adventures and tabletop aids existing together. A player could explore a fully computerized Forgotten Realms adventure in one product while using another computer program to prepare a conventional campaign controlled by a human Dungeon Master.
That approach is visible even in the language of the manuals. Volume I stated that it could not replace carefully designed major encounters. Volume II similarly described itself as an enhancement to TSR’s paper products.
The computer was supposed to handle repetition, record keeping, randomization, and data retrieval. Imagination, judgment, storytelling, and campaign design remained with the Dungeon Master.
A Series That Stopped After Two Volumes
The early SSI announcements described Dungeon Master’s Assistant as a series, and the original concept was broad enough to support additional utilities.
Only two principal volumes emerged.
Volume I covered encounters. Volume II covered characters and treasure. By the beginning of the 1990s, SSI’s AD&D catalog increasingly centered on conventional computer games, including Gold Box role-playing adventures, action titles, strategy games, and eventually first-person RPGs such as Eye of the Beholder.
The surviving 1991 SSI catalog still listed the first Dungeon Masters Assistant, showing that the utility had a commercial life beyond its initial release. Yet a third major volume did not join the line.
The surviving documentation does not provide a simple explanation for why the planned series stopped where it did, and it would be dangerous to invent one. What the record clearly shows is that SSI experimented seriously with the concept, released two substantial utilities, supported them across major home-computer platforms, and sold them alongside some of the most important licensed computer RPGs of their era.
An Early Digital Companion to Tabletop Role-Playing
The historical importance of Dungeon Masters Assistant is easiest to see when the program is viewed on its own terms.
It was not an unsuccessful attempt to make an AD&D video game because it was never supposed to be one. Its packaging, manuals, advertisements, catalogs, and contemporary reviews repeatedly described it as a utility.
That makes it an unusually early example of a digital companion for a tabletop role-playing system.
Modern role-playing groups routinely use computers and phones for searchable rules, automated character sheets, random encounter generators, treasure generators, campaign databases, dice rollers, initiative trackers, map software, and virtual tabletops. Some groups play entirely online, while others remain gathered around a physical table but use digital tools throughout the session.
Dungeon Masters Assistant did not offer that modern level of convenience. A Commodore 64 owner could encounter slow loading, disk swapping, limited interfaces, and a database that contemporary critics found cumbersome. Those limitations were real.
The underlying idea, however, was remarkably recognizable.
Let the computer remember the tables. Let it perform repetitive calculations. Let it generate the raw material. Let it print or save the information. Then let the Dungeon Master decide what happens when the adventurers open the door.
In the late 1980s, when SSI and TSR were still discovering what an official Dungeons & Dragons computer product could be, Dungeon Masters Assistant offered one answer that did not require replacing the tabletop at all.
It simply pulled up a chair beside it.
Sources & Further Reading
Strategic Simulations, Inc. Dungeon Masters Assistant, Volume I: Encounters. User manual. Sunnyvale, CA: Strategic Simulations, Inc., 1988. https://mocagh.org/ssi/dmassist1-manual.pdf
Strategic Simulations, Inc. Dungeon Masters Assistant, Volume II: Characters & Treasures. User manual. Sunnyvale, CA: Strategic Simulations, Inc., 1989. https://www.mocagh.org/ssi/dmassist2-manual.pdf
Strategic Simulations, Inc. Fall 1988/Winter 1989 Product Catalog. Sunnyvale, CA: Strategic Simulations, Inc., 1988. https://www.mocagh.org/ssi/ssi-88-89catalog.pdf
Strategic Simulations, Inc. 1989–1990 Product Catalog. Sunnyvale, CA: Strategic Simulations, Inc., 1989. https://mocagh.org/ssi/ssi-89-90catalog.pdf
Strategic Simulations, Inc. 1991 Product Catalog. Sunnyvale, CA: Strategic Simulations, Inc., 1991. https://www.mocagh.org/ssi/ssi-91catalog.pdf
Strategic Simulations, Inc. “SSI Presentation to TSR for Dungeons & Dragons License.” Spring 1987. Box 1, Folder 5, Joel Billings’ Strategic Simulations, Inc. Papers, Collection 112.1517. Brian Sutton-Smith Library and Archives of Play, The Strong National Museum of Play, Rochester, NY. See collection finding aid: https://museumofplay.org/app/uploads/2021/09/Finding-Aid-to-Joel-Billings-Strategic-Simulations-Inc.-SSI-papers_052115.pdf
The Strong National Museum of Play. Finding Aid to the Joel Billings’ Strategic Simulations, Inc. (SSI) Papers, 1976–2001. Collection 112.1517. Brian Sutton-Smith Library and Archives of Play. https://museumofplay.org/app/uploads/2021/09/Finding-Aid-to-Joel-Billings-Strategic-Simulations-Inc.-SSI-papers_052115.pdf
The Strong National Museum of Play. Dungeons & Dragons-Related Materials in the Brian Sutton-Smith Library and Archives of Play. Rochester, NY: The Strong National Museum of Play. https://museumofplay.org/app/uploads/2021/09/Dungeons-Dragons-related-materials_Library-and-Archives_051619.pdf
Strategic Simulations, Inc. “AD&D Computer Products Update.” Inside SSI, Summer 1987. Preserved in “SSI & TSR,” History of SSI Games. https://sites.google.com/site/ssihistory/ssi-tsr
Strategic Simulations, Inc. “AD&D Computer Products March Toward Release.” Inside SSI, Winter 1987. Preserved in “SSI & TSR,” History of SSI Games. https://sites.google.com/site/ssihistory/ssi-tsr
Lesser, Hartley, and Patricia Lesser. “The Role of Computers.” Dragon, no. 127 (November 1987). https://pied.nu/dragon/files/Drmg127.pdf
“Advanced Dungeons & Dragons Computer Products.” Dragon, no. 138 (October 1988). https://pied.nu/dragon/files/Drmg138.pdf
Strategic Simulations, Inc. Advertisement for Dungeon Masters Assistant, Volume I: Encounters. COMPUTE!, no. 102 (November 1988). https://colorcomputerarchive.com/repo/Documents/Magazines/Compute%20%28Clean%29/Compute_Issue_102_1988_Nov.pdf
Strategic Simulations, Inc. Advertisement for Dungeon Masters Assistant, Volume I: Encounters. RUN, no. 59 (November 1988). https://www.c64brain.com/wp-content/uploads/2022/01/run_issue_59_1988_nov.pdf
Strategic Simulations, Inc. Advertisement for Dungeon Masters Assistant, Volume I: Encounters. Computer Gaming World, no. 56 (February 1989). https://www.cgwmuseum.org/galleries/issues/cgw_56.pdf
“Dungeon Masters Assistant Volume I: Encounters.” Computer Entertainer 7, no. 6 (September 1988). https://www.ataricompendium.com/archives/newsletters/video_game_update/computer_entertainer_sep88.pdf
Ryan, John. Review of Dungeon Masters Assistant, Volume I: Encounters. RUN, no. 64 (April 1989). https://www.commodore.ca/wp-content/uploads/2016/01/run_issue_64_1989_apr-www.commodore.ca.pdf
Trunzo, Jim. “The Silicon Dungeon.” White Wolf, no. 16 (June–July 1989): 50.
Review of Dungeon Masters Assistant Volume I: Encounters. INFO, no. 24 (January–February 1989).
Dragon, no. 145 (May 1989). Reader and editorial discussion of Dungeon Masters Assistant. https://pied.nu/dragon/files/Drmg145.pdf
Strategic Simulations, Inc. Advertisement for Dungeon Masters Assistant, Volume II: Characters & Treasures. Dragon, no. 150 (October 1989). https://pied.nu/dragon/files/Drmg150.pdf
Strategic Simulations, Inc. Advertisement for Dungeon Masters Assistant, Volume II: Characters & Treasures. RUN, no. 71 (November 1989). https://www.commodore.ca/wp-content/uploads/2016/01/run_issue_71_1989_nov-www.commodore.ca.pdf
Strategic Simulations, Inc. Advertisement for Dungeon Masters Assistant, Volume II: Characters & Treasures. RUN, no. 72 (December 1989). https://www.commodore.ca/wp-content/uploads/2016/01/run_issue_72_1989_dec-www.commodore.ca.pdf
Strategic Simulations, Inc. Advertisement for Dungeon Masters Assistant, Volume II: Characters & Treasures. Dragon, no. 152 (December 1989). https://pied.nu/dragon/files/Drmg152.pdf
“Dungeon Masters Assistant Volume II: Characters & Treasures.” COMPUTE!’s Gazette, December 1989.
“Dungeon Masters Assistant Volume II: Characters & Treasures.” Computer Entertainer 8, no. 9 (December 1989).
Museum of Computer Adventure Game History. “Strategic Simulations, Inc.: Advanced Dungeons & Dragons TSR Series.” Accessed November 1, 2026. https://www.mocagh.org/loadpage.php?getcompany=ssi&npp=25&series=Advanced+Dungeons+and+Dragons+TSR+Series&start=0&whatsnew=0
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Eli’s Software Encyclopedia. “Dungeon Masters Assistant Volume I (Apple II, 5 1/4″ Disk), Strategic Simulations, Inc., 1988 USA, Canada Release.” Accessed November 1, 2026. https://elisoftware.org/wiki/Dungeon_Masters_Assistant_Volume_I_%28Apple_II%2C_5_1/4%22_Disk%29_Strategic_Simulations%2C_Inc._-_1988_USA%2C_Canada_Release
Eli’s Software Encyclopedia. “Dungeon Masters Assistant Volume II (Apple II, 5 1/4″ Disk), Strategic Simulations, Inc., 1989 USA, Canada Release.” Accessed November 1, 2026. https://elisoftware.org/wiki/Dungeon_Masters_Assistant_Volume_II_%28Apple_II%2C_5_1/4%22_Disk%29_Strategic_Simulations%2C_Inc._-_1989_USA%2C_Canada_Release
Eli’s Software Encyclopedia. “Dungeon Masters Assistant Volume II (C64, 5 1/4″ Disk), Strategic Simulations, Inc., 1989 USA, Canada Release.” Accessed November 1, 2026. https://elisoftware.org/wiki/Dungeon_Masters_Assistant_Volume_II_%28C64%2C_5_1/4%22_Disk%29_Strategic_Simulations%2C_Inc._-_1989_USA%2C_Canada_Release
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History of SSI Games. “SSI Games: D through K.” Accessed November 1, 2026. https://sites.google.com/site/ssihistory/Home/ssi-games-d-through-k
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